a man and woman on a date. he is talking about his career in an interesting and engaging way.

How to Talk About Your Career Without Boring Your Date

As a high-level executive, your career is a big part of your life, and naturally, you’ll want to talk about it when you’re on a date. But how do you share this important part of yourself without sounding like you’re giving a TED Talk or turning the conversation into a one-sided interview? The key is striking a balance between talking about your work in a way that’s engaging and ensuring your date is involved and interested.

Let’s break down how to do that:

Tell Stories, Not Facts

Nobody wants to feel like they’re reading a résumé during a date. The best way to make your career interesting to someone who may not work in your industry is to tell stories. Everyone loves a good story—especially one that’s entertaining, funny, or reveals a deeper aspect of who you are.

For example, instead of saying, “I manage a team of 50 people,” you could share a story about a time you helped your team overcome a challenge or an unusual situation that happened in the office. Stories add personality to your career and give your date a chance to relate on a human level, even if they don’t understand all the technical aspects of your work.

Remember, it’s less about the details and more about the experience. Focus on how these moments made you feel, how you handled them, and what you learned. This makes the conversation feel more personal and less like a job interview.

Focus on the Relatable Stuff

Your date might not know the intricacies of your job, but they can still understand and relate to some aspects of it. This is where you can highlight the universal themes in your work. Talk about teamwork, leadership, balancing work and personal life, or overcoming obstacles.

For instance, instead of diving into the complexities of a recent project, you might say, “One of the biggest lessons I’ve learned is how to manage stress when deadlines are tight. I’ve had to figure out how to stay calm and keep my team focused, even when things feel overwhelming. It's made me a great partner for game nights!”

“One of the biggest lessons I’ve learned is how to manage stress when deadlines are tight. I’ve had to figure out how to stay calm and keep my team focused, even when things feel overwhelming. It's made me a great partner for game nights!”

Themes like stress management, problem-solving, or learning to work with different types of people are universally relatable. This makes it easier for your date to connect with what you’re saying, regardless of their own career path.

Keep It Short and Sweet

When talking about your career, it's important to keep things concise and be aware of how your date is responding. Share a few key points, then check in with your date—both through their verbal responses and their body language. If they’re leaning in, asking questions, or showing curiosity, feel free to expand a little more. But if they seem disengaged or are giving short responses, it’s a good time to shift the conversation.

You don’t have to go into every detail of your job or explain every project you've worked on. It’s okay to give a brief overview and then let the conversation move on to another topic. Think of it as giving a highlight reel, not a documentary. Your date will likely appreciate a balanced conversation where both of you get to share and listen.

Make It a Conversation, Not a Lecture

The last thing you want to do is turn the date into a lecture about your job. Instead, aim to make it a two-way conversation. After sharing something about your career, ask your date questions about their experiences or thoughts. This not only makes the conversation more dynamic, but it also shows that you’re genuinely interested in getting to know them.

For instance, after talking about how you handle leadership challenges, you could ask, “Have you ever had to deal with a difficult situation at work? How did you handle it?” Or, if you’re discussing work-life balance, you might ask, “What’s your approach to managing stress in your own job?”

By engaging your date, you create a more balanced and interactive conversation, making it easier for both of you to connect.

Show the Human Side

Your career isn’t just about what you do—it’s about how it has shaped who you are. Instead of focusing solely on the job's technical aspects, share how your work experiences have influenced you personally.

For example, you might explain how a challenging project helped you develop resilience, or how leading a team has taught you patience and empathy. This brings a deeper layer to the conversation and helps your date see beyond the job title to who you are as a person.

People connect through shared human experiences, so don’t be afraid to talk about how your work has affected your personal growth, values, or the way you see the world.

Skip the Business Jargon

One of the quickest ways to lose someone’s attention is by using jargon they don’t understand. Even if your date is polite and nods along, they’re likely not following if you’re using industry-specific terms or technical language.

Keep it simple. Instead of going into the nitty-gritty of your field, explain things in layman’s terms. If you find yourself slipping into jargon, take a step back and rephrase. For example, instead of saying, “I’m responsible for overseeing the cross-functional integration of department workflows,” you could say, “I help different teams work together smoothly on big projects.”

“I help different teams work together smoothly on big projects.”

This ensures your date doesn’t feel lost or confused, making it easier for them to stay engaged in the conversation.

Switch the Focus to Common Interests

Once you’ve shared a bit about your job, don’t linger too long on the subject. Transition into topics you both enjoy. Ask about your date’s interests, hobbies, or experiences. Finding common ground makes the conversation more enjoyable for both of you and keeps things from feeling too work-centric.

For example, if your date mentioned earlier that they love hiking, you could say, “It sounds like you’re really into the outdoors—what’s your favorite hiking spot?” This shifts the conversation to something you can both explore together and keeps things balanced.

Remember, dates are about getting to know each other as people, not just as professionals.

Add a Little Humor

If your job has some funny or unexpected moments, don’t hesitate to share those! Humor is a great way to keep things light and fun, especially when talking about work.

For example, you might recount a time when a meeting went hilariously wrong or share a quirky office tradition. People appreciate humor, and it can make even work-related topics more engaging. Just make sure the humor is appropriate for the conversation and isn’t overly self-deprecating or too focused on inside jokes from your industry.

Final Thoughts

Talking about your career on a date can be tricky, but it doesn’t have to be boring. By focusing on storytelling, keeping things relatable, and engaging your date in the conversation, you can share this important part of your life without losing their interest. Remember to keep things balanced, show your personality, and have fun with it—after all, dates are about connection and enjoyment!


a shadowy figure sits behind a laptop. they are involved in dating scams.

The Dating Scams Executives Fall For—And How to Avoid Them

In an increasingly digital world, scammers are constantly finding new ways to target individuals, especially those with substantial wealth. These scams often exploit the desire for love, connection, or exclusive opportunities, making them emotionally and financially devastating.

Knowing the red flags and how to protect yourself is crucial. This guide will walk you through some of the most common scams targeting executives and provide actionable steps to help you stay safe.

Romance Scams

Romance scams are one of the most prevalent and emotionally devastating scams targeting wealthy individuals. They typically prey on people seeking companionship or love online.

Scammers typically use fake profiles on dating sites or social media, often using stolen photos. They portray themselves as attractive and successful people seeking a serious relationship.

Over time, they build a relationship with the victim, sometimes waiting weeks or months. This is a ploy to gain their victim’s trust before asking for money under false pretenses.

What to Look Out For

  • Fake Profiles: Scammers create an appealing online persona, often claiming to be working or living abroad.
  • Emotional Bonding: The scammer spends weeks or even months cultivating a relationship with the victim, expressing deep affection or love and building trust. They often claim to be living or working abroad, making it difficult to meet in person.
  • Fabricated Emergencies: Once trust is established, the scammer invents a crisis or emergency, such as needing money for a medical bill, travel expenses to visit the victim, or help with a business deal gone wrong.
  • Requests for Money: The scammer may ask for money to be sent via wire transfer, gift cards, or cryptocurrency, which are hard to trace and recover.
  • Gradual Escalation: The initial requests for money may be small, but over time, they escalate, with the scammer finding new reasons to request larger amounts. The victim, emotionally invested, is often willing to comply.
  • Disappearing Act: After receiving a significant sum, the scammer may disappear, leaving the victim heartbroken and financially harmed.

Example: A wealthy woman meets someone online who seems perfect: he’s successful, attractive, and shares many of the same interests. After several months of communicating, the scammer claims he's finally ready to meet in person, but he’s in a financial bind.

He asks the woman to pay for his travel expenses. She’d given him a few dollars here and there, so it wasn’t a big deal to ask her for this favor.

The victim, eager to meet her potential partner, sends the money to his direct payment account, only to be ghosted.

What You Can Do to Avoid Romance Scams

  • Be cautious of anyone who quickly professes love or affection online.
  • Never send money to someone you haven’t met in person.
  • Be skeptical of requests for financial assistance, no matter how convincing the story.
  • Do a reverse image search of the person’s photos to see if they appear elsewhere on the internet.

Sugar Daddy/Sugar Baby Scams

Sugar daddy or sugar baby scams involve individuals posing as attractive young people (sugar babies) seeking a mutually beneficial relationship with a wealthy individual.

These scams are different from other romance scams because the victim is aware of the scammer’s intention to take money from them. The scammer’s dishonesty about their identity and/or their intention to invest in a romantic connection is what makes this a scam.

What to Look Out For

  • Fake Profiles: The scammer creates an attractive profile, often using stolen photos and a fabricated backstory. They appeal to the victim by promising companionship, affection, or intimacy in exchange for financial support.
  • Requests for Upfront Payments: The scammer may ask for money to cover expenses like rent, tuition, or travel before any in-person meeting occurs. They might also request gifts or prepaid cards.
  • Subscription Scams: Some scammers create fake sugar dating websites that charge high membership fees for access to "exclusive" profiles. Once the victim pays, they may find that the profiles are fake or that they receive little to no interaction.
  • Disappearing After Payment: After receiving money or gifts, the scammer often disappears, breaking off contact with the victim. They may also string the victim along with promises of future meetings that never happen.

Example: A wealthy man is approached online by someone claiming to be a college student looking for financial support in exchange for companionship. The man becomes emotionally invested in this relationship, and he’s led to believe she is, too.

They chat for a few months but are never able to meet in person. Still, he happily sends money for anything she needs. After receiving a significant amount of money to cover rent and expenses, the man asks again when they can meet as promised.

The sugar baby suddenly stops responding and deletes her profile, never to be seen again.

What You Can Do to Avoid Sugar Daddy/Sugar Baby Scams

  • Before engaging in any financial exchange, verify the person’s identity. Use video calls or meet in person in a safe, public place to ensure they are who they claim to be.
  • Be cautious of anyone asking for money before meeting in person.
  • Don’t share personal details such as your home address, financial information, or workplace until you’ve built a substantial level of trust.

Blackmail and Sextortion

Blackmail and sextortion scams involve scammers luring wealthy individuals into compromising situations, often through explicit conversations, photos, or videos. Once the scammer has incriminating material, they threaten to release it unless the victim pays a significant sum of money.

What to Look Out For

  • Initial Attraction: The scammer seduces the victim through flirtation or intimate conversation, encouraging them to share explicit photos, videos, or engage in compromising behavior.
  • Gathering Material: Once the scammer has sufficient compromising material, they reveal their true intentions, threatening to share the content with the victim's family, friends, or business associates.
  • Extortion Demands: The scammer demands money, often in the form of wire transfers, gift cards, or cryptocurrency, to keep the material private. They may continue to extort the victim, knowing that the fear of exposure is a powerful motivator.
  • Continued Threats: Even if the victim pays, the scammer may continue to threaten them, demanding more money over time.

Example: A wealthy business executive begins an online relationship with someone they believe to be a romantic interest. After sharing intimate photos, the scammer reveals that they’ve recorded the interactions and will send the photos to the executive’s colleagues unless they pay a large sum.

What You Can Do to Avoid Blackmail and Sextortion

  • Be cautious about sharing explicit photos, videos, or engaging in intimate conversations online, especially with someone you haven’t met in person.
  • Use platforms with strong privacy settings and encryption. Be aware that even secure platforms can be compromised.
  • If you suspect someone is trying to blackmail you, report it to the platform where you met and consider involving law enforcement.
  • If you’re targeted, avoid paying the scammer. Giving into demands often leads to further extortion attempts.

Online Dating Scams

Fake dating services or matchmaking scams target wealthy individuals who are willing to pay a premium for access to exclusive dating pools. Scammers create or operate fraudulent matchmaking services, promising introductions to elite singles but failing to deliver on these promises.

What to Look Out For

  • High-End Appeal: The scammer advertises their service as a high-end online dating service catering to wealthy, successful individuals. They claim to have access to a pool of elite singles.
  • Fees: The victim is charged a large upfront fee for membership, with promises of personalized matchmaking, exclusive events, and introductions to high-quality partners. The fees can range from thousands to tens of thousands of dollars.
  • Fake Profiles: In some cases, the site may show the victim a few fake profiles of attractive, successful people who either don’t exist or are not part of the service. The goal is to get them to pay for a profile of their own.

Example: A wealthy individual signs up for an exclusive online dating service that promises access to high-caliber professionals. After paying a substantial fee, they receive access to a database full of profiles.

Several are obviously fake; they have one or two stolen photos of a model, or they have a bio section full of nonsense. Others might be real, but they’re far from the high-caliber professionals the site promises.

What You Can Do to Avoid Online Dating Scams

  • Be cautious of profiles with limited information, professional photos, or people who avoid video calls or meeting in person.
  • Be wary of services that require large upfront payments. Consider starting with free or lower-tier memberships to evaluate the service first.

Other Scams Executives Should Know About

Dating scams aren’t the only places where executives should exercise caution. Unfortunately, scams are prevalent in most areas of our lives, especially where money and emotions collide. Here are some other things to watch out for:

Investment Scams

Investment scams lure victims with promises of high returns with little or no risk. These scams can take various forms, from Ponzi schemes to fraudulent cryptocurrency investments. The scammer often creates a sense of urgency to pressure the victim into making a quick decision without fully investigating the opportunity.

What to Look Out For

Ponzi Schemes: Scammers pay returns to earlier investors using the capital of new investors, rather than from profit earned by the operation. The scheme collapses when there are not enough new investors.
Pyramid Schemes: Similar to Ponzi schemes, but victims are recruited to invest with the promise of recruiting others to earn returns. The focus is on recruitment rather than actual products or services.
Fake Cryptocurrency Investments: Scammers create fake cryptocurrency exchanges or offer non-existent tokens. They may also promote initial coin offerings (ICOs) that are fraudulent.

What You Can Do to Avoid Investment Scams
  • Be skeptical of any investment that guarantees high returns with no risk.
  • Research the investment opportunity thoroughly.
  • Avoid investments where you don’t fully understand how they work.
  • Verify the legitimacy of the investment with regulatory bodies like the SEC.

Phishing Scams

Phishing scams are one of the most common and dangerous types of online fraud. Scammers create fake emails, messages, or websites that closely mimic those of legitimate companies, such as banks, e-commerce platforms, or social media sites. The goal is to trick victims into clicking on malicious links, downloading harmful attachments, or providing sensitive information like usernames, passwords, or credit card numbers.

What to Look Out For
  • Email Phishing: A scammer sends an email that looks like it's from a trusted source, such as your bank. The email may ask you to verify your account information or warn you about a problem that requires urgent action. The provided link directs you to a fake website designed to capture your login details.
  • Spear Phishing: A more targeted version of phishing, where the scammer personalizes the message by using information specific to the victim, making it harder to detect as a scam.
  • Clone Phishing: Scammers copy legitimate emails and replace links or attachments with malicious ones. The email may appear as a resend of an earlier legitimate communication.
What You Can Do to Avoid Phishing Scams
  • Be wary of unsolicited emails asking for personal information.
  • Check the sender's email address for any discrepancies.
  • Hover over links to see the actual URL before clicking.
  • Use two-factor authentication for added security.

Charity Scams

Charity scams exploit the goodwill of people who want to help others, particularly after natural disasters or during the holiday season. Scammers create fake charities or impersonate real ones to solicit donations, which never reach the intended beneficiaries.

What to Look Out For
  • Impersonating Legitimate Charities: Scammers use names and logos of well-known charities, often slightly altered, to trick people into donating.
  • Fake Charities: The scammer creates a completely fake charity, often with a website that looks legitimate, to collect donations.
  • Urgency Tactics: Scammers often create a sense of urgency, claiming that funds are needed immediately to help victims of a recent disaster.
What You Can Do to Avoid Charity Scams
  • Donate directly through the official website of a known charity.
  • Research the charity using resources like Charity Navigator or the BBB Wise Giving Alliance.
  • Be cautious of unsolicited donation requests, especially via email or social media.
  • Verify that the charity is registered and legitimate.

Business Email Compromise (BEC)

Business Email Compromise (BEC) is a sophisticated scam targeting businesses. Scammers gain access to a company’s email accounts, often through phishing, and then impersonate executives or trusted partners to trick employees into making unauthorized wire transfers or disclosing sensitive information.

What to Look Out For
  • Email Spoofing: The scammer sends emails that appear to come from a company executive, such as the CEO or CFO, requesting an urgent wire transfer.
  • Account Takeover: Scammers gain control of a legitimate email account and use it to request payments or sensitive information.
  • Vendor Impersonation: Scammers impersonate a company’s suppliers or partners and request changes to payment details, directing funds to their own accounts.
What You Can Do to Avoid Business Email Compromise
  • Implement strict protocols for verifying payment requests, especially if they involve changes to payment details.
  • Train employees to recognize phishing attempts and suspicious email activity.
  • Use multi-factor authentication and regularly update passwords.
  • Verify requests for money or sensitive information with a phone call or in-person confirmation.

Staying vigilant and informed is your best defense against these types of scams. Wealthy individuals are often prime targets due to their financial resources, but with the right precautions, you can significantly reduce your risk.

Always prioritize your safety over the allure of love, financial gain, or exclusive opportunities. By being cautious, verifying identities, and understanding the tactics scammers use, you can protect both your heart and your assets from potential harm.


a man and woman who are dating with a difference in age. he is around 15 years older than she is. they are smiling happily at one another.

Dating with a Difference in Age: Does it Really Matter?

Does a difference in age make a relationship different?

Well, it depends on whom you ask.

For most outsiders, relationships with significant age differences tend to raise eyebrows. However, for many couples, the fear of judgment isn’t enough to deter their pursuit of true love.

Amongst celebrities, age gap relationships are quite normalized. George and Amal Clooney, for example, share a 17 year age difference; Jay-Z is 12 years senior to his wife, Beyoncé; and Catherine Zeta-Jones is famously 25 years younger than her husband, Michael Douglas.

With so many examples of age-gap success stories, dating with an age difference can’t be that bad, right?

Well, for most couples, dating with a significant difference in age can be tricky.

Want to know the age-gap impact on the quality and longevity of a relationship? Let’s break it down.

The Numbers Game

Is age really just a number?

For many couples, a few years’ difference is nothing out of the ordinary. Approximately 8.5 percent of the population is comprised of couples with an age gap ranging from 5 to 15 years.

If it seems like the age difference usually yields towards an older man with a younger woman, that’s because it’s true. Statistically, male partners take the lead in the age department. Only 1.3 percent of couples are composed of an older woman with a younger man.

Some theories make sense of this gendered phenomenon by looking back at our ancestors. The theory goes that, by the time the female partner reaches her prime reproductive years, she is naturally more attracted to a man who has accumulated the status and resources necessary to support a family. That takes some time.

Many studies show that singles tend to be generally open-minded about age differences when it comes to their own relationship preferences. At least, to a certain degree. However, it becomes much easier to pass judgment when it comes to other people’s relationships.

Research shows that society tends to object to couples with an obvious difference in age. Well-meaning or not, disapproval from friends and family members often causes age-gap couples to feel isolated and misunderstood.

Mind the Gap

At what point does an age difference become too different?

Most researchers agree that an "age gap" relationship is when one partner is at least 10 years older than the other.

According to one study, age-gap couples report higher levels of dissatisfaction within their relationship. The larger the age gap, the more likely the couple is to divorce. Often, breakups between these couples can be traced back to their age imbalance.

Does that mean age-gap relationships are doomed to fail? Definitively not. But, if you’re dating with a difference in age, you’ll likely face unique challenges that could be avoided by pursuing someone within your own generation.

Cultural Differences

Couples born in different generations tend to have an equally as different frame of reference on reality. This goes for everything from world views to inside jokes.

The larger the age difference between two partners, the less likely it is that they will understand the nuances of each other’s generation. Things like pop culture references, life experiences, and hobbies are often distinct to one’s generation.

Younger partners might also have more progressive views about society, politics, and relationship values. They might consider older partner’s opinion’s to be too traditional or constricting.

While these things may seem like small differences, couples who cannot connect on a cultural level may find it harder to talk to one another or find common ground throughout their relationship.

Power Trip

They say time is money, and often that stays true when one partner is older in a relationship.

Along with life experience, older partners tend to have more financial means than younger partners.

At the beginning of a relationship, having a partner who can take care of you both financially and emotionally might feel great. Eventually, however, the relationship can turn into a dynamic that feels controlling to the other partner.

A gap in both wealth and age can create an exponential difference in power within a relationship. An older partner could use their financial superiority to exert control over a significantly younger spouse. This would cause tension in the relationship and make one partner experience the conflicting feelings of both dependency and resentment towards the other.

Sweetheart or Sugar Daddy?

One of the reasons relationship age differences remain such a cultural taboo is due to the “gold-digger” stereotype. These relationships are viewed as more transactional, with one partner seeking out the other more for their money than their love.

Cliche? Yes. But, that doesn’t mean it doesn’t really happen.

Some statistics point towards a disproportionate shift in older, wealthy married men to younger women. While it’s impossible to judge the motivations for each partner, it’s something worth thinking about before rushing into commitment with someone much younger.

Of course, not every relationship with a significant age difference is predatory. Sometimes, the worst exploitation can happen between peers. However, couples that share a big difference in age should keep an eye out for red flags.

Life stages

When it comes to planning for the future with your partner, it’s important that you two are on the same page. This becomes difficult if you two are in two completely different stages of your lives.

For example, a younger partner might be entering into a relationship with the expectation of getting married, having children, and starting a family with their partner. If their partner is significantly older, it’s possible that they’ve already experienced these things with a previous relationship, and not want to have more children or risk going through another divorce.

On the other hand, an older partner might want marriage and kids, but feel like their biological clock is ticking. Sensing that they are running out of time, they might unknowingly pressure their partner to commit or have children before they are ready.

The Closer, the Better

Is any gap acceptable?

Studies show that the closer a couple is in age, the better. Couples who are within a three year age difference reported higher levels of satisfaction with their partners, and stayed together longer than those with a ten year gap or more.

Still considering an age-gap relationship? Ask yourself:

  • Is this a long-term relationship?
  • Do we share the same long-term goals?
  • Do we agree about whether or not we want children?
  • Do we have the support of our friends and family?

If you answered ‘no’ to one or more of these questions, the difference in age might just be the make-or-break factor in your relationship.


a man and woman having conversation at a restaurant table. they are askng appropriate questions for a second date.

Questions to Ask on a Second Date

So, you made it past the first date and things went well! Making it to the second date is an exciting step! The initial jitters are gone, and now it's time to get to know each other a bit better. A second date is the perfect opportunity to dig a little deeper and see if there’s a real connection.

But what do you ask? If your questions are too surface-level, you might never make it past small talk. However, you also run the risk of asking a question that’s far too personal for a second date if you’re not careful.

For the second date, these questions can be slightly more personal, but they don’t ask for your date to reveal anything too intimate about themself. This is the kind of question that is perfect for a second date, allowing you to deepen your connection without getting too intense. Use this post as inspiration for when you’re trying to keep the conversation going, or to fill an awkward silence.

Questions About Relaxation and Leisure

Understanding how your date likes to relax and spend their weekends provides insights into their lifestyle and compatibility with your own. These questions help you see if your downtime habits align and if you can envision spending leisure time together harmoniously. It’s a great way to discover common interests and find activities you might enjoy together.

  • What's your favorite way to relax after a long day?
  • What's your favorite way to spend a weekend?
  • Is there a hobby or interest you’ve recently picked up?

"What's your favorite way to relax after a long day?"
Everyone has their own way of unwinding. This question can give you insight into their self-care routines and what they find comforting. Plus, it might give you ideas for future relaxing activities together.

Questions About Values and Influences

These questions explore the values and influences that shape your date’s life. They can lead to meaningful conversations about personal growth, priorities, and what they cherish in relationships. It’s a great way to see if your core values align and to connect on a deeper level.

  • What's the best advice you’ve ever received?
  • If you won the lottery tomorrow, what would you do?
  • I’d love to know more about your friends.
  • What's the most interesting book you’ve read?
  • What do you value most in friendships?
  • What's a cause or charity that’s important to you?
  • What are you passionate about?

"If you won the lottery tomorrow, what would you do?"
This question is fun and imaginative. It can reveal a lot about your date’s priorities and how they might handle a sudden windfall. Whether they’d travel the world, start a business, or give to charity, it’s an interesting way to see what they value.

Questions About Personal Achievements and Aspirations

Discussing personal achievements and future aspirations allows your date to share significant moments and dreams with you. It shows that you’re interested in their journey and future goals, fostering a sense of support and encouragement in your budding relationship.

  • What's something you’re really proud of?
  • What's one thing you’ve always wanted to try but haven’t yet?
  • What's something not career-related on your bucket list?
  • What accomplishment outside of your career has given you the most satisfaction?
  • If you had a month off with no responsibilities, how would you spend it?
  • Where do you see yourself in five years in terms of personal growth and well-being?

"What’s something you’re really proud of?"
Everyone has accomplishments they’re proud of, whether big or small. This question allows your date to share a significant moment in their life, giving you a glimpse into their achievements and what they value.

Fun and Playful Questions

These questions add a playful element to your date, making the conversation lively and entertaining. Discovering hidden talents and favorite meals can lead to fun stories and maybe even plans for a karaoke night or a culinary adventure.

  • What's your go-to karaoke song?
  • Do you have any hidden talents?
  • What's your dream vacation?
  • What's the best meal you’ve ever had?
  • Do you have any travel traditions or rituals?

"What’s your go-to karaoke song?"
This is a fun and playful question that can lead to some laughs. Even if your date isn’t a singer, everyone has that one song they’d belt out in a karaoke bar. It’s a light-hearted way to share music tastes and maybe even plan a future karaoke night.

Rules for Asking Questions on a Date

When asking questions on a second date, keep things genuine and light-hearted. Show real interest in your date by listening actively and sharing your own stories too. Avoid overly personal or controversial topics to keep the mood positive and fun. Respect boundaries and pay attention to body language to ensure your date is comfortable. Aim for a balanced conversation where both of you can share and connect. By being present and attentive, you can make your second date enjoyable and meaningful, setting the stage for a deeper connection.

These questions are designed to help you move beyond small talk and get to know your date on a more personal level while still respecting more private or controversial topics. Every conversation is a two-way street, so remember to share your own experiences and thoughts as well. Keep it light, engaging, and genuine, and you’ll have a second date to remember.


a man and woman in love, dancing together on a city street. they are learning to make time for their relationship.

How to Make Time for a Relationship

They say time is the best gift you could ever give someone because you are essentially sharing a piece of your life with them that you can never get back. Seeing as how my primary Love Language is Quality Time, I tend to agree. So, how do you make time for a relationship when you’re being pulled in a hundred different directions?

One of the most common complaints among couples is that their partner doesn’t put enough time or effort into the relationship to the point that it has become completely one-sided

We find time for the things that matter most to us in life. If you want to prioritize your relationship, you have to start finding time to focus on your partner. 

Set Your Priorities

We all have a finite amount of time, and the way we choose to spend it says a lot about what we value. In a world where we're constantly juggling work, family, social obligations, and personal interests, it's easy to let our relationships take a backseat. But if a loving partnership is important to you, prioritizing what truly matters is essential.

First and foremost, assess your commitments and identify the other non-negotiables. Maybe it's your job, your kids, or a personal passion. Once you've established these, look at your schedule and find where you can carve out time for your relationship.

It's about making deliberate choices. If your relationship is a priority, then treating it as such in your daily life is crucial. You might have to sacrifice a few hours of Netflix or delegate a work task, but the reward is a deeper, more meaningful connection with your partner.

This is also about setting boundaries. Sometimes, saying "no" to less important engagements can free up time for the people who matter most. This doesn't mean neglecting other aspects of your life, but rather finding a balance that allows you to invest in your relationship. It could be as simple as scheduling a regular date night or as significant as planning a vacation to reconnect.

Organize Regular Outings

We’re all busy with work, travel, and family responsibilities; if you can’t fit a date into your calendar every week, then make up for it by whisking her off for a weekend getaway.

We all experience ruts in our relationships from time to time. Things start to feel monotonous and boring. Sound familiar? Try getting out of your routine. Instead of going to the same places all the time, try that spicy new spot that just opened up. Attend a pop-up art exhibit. Learn a new sport or skill together. 

The point is, if being in love is important to you, then you have to make time for a relationship in your life. If you need to delegate some projects to ensure you’re out of the office on time every Friday night, then do it. 

A good way to encourage more date nights is to buy season tickets somewhere. If it’s already paid for, and you know you have an empty box waiting on you, you’re more likely to find time to go.

And yes, if necessary...pencil in intimacy. It’s not sexy to put it on the calendar, but if that’s the only way to guarantee it happens, then write it in big letters and underline it in red. 

Forget Your Phones

Being a busy person in a relationship often means maximizing the little time you're able to spend together. The key word of Quality Time is quality. It’s impossible to feel in tune with someone who is more focused on iTunes. When you're together, try to put away distractions and focus on one another.

We’re addicted to our devices enough as it is. If you find yourself reaching for your devices during quality time more often than you'd like, try instituting a no-phones rule for certain activities, like during mealtimes. This removes the temptation and allows you to focus on one another more easily.

From sleep to sex, studies show there are countless reasons why leaving your phone outside of the bedroom at night is a good idea, as well. You should also think about banning them from coming out too often on date nights. In the early stages of a relationship, you don’t always get to spend the amount of time with your significant other that you want, so you have to make the most of the time you do get. 

Carve Out Time for Communication

Whenever possible, go to bed together at the same time and include communication as part of your nightly routine. Living together can make it easier to take your time together for granted, but a nightly check-in can serve as a reminder to appreciate one another. While you’re getting ready for bed and snuggling in for the night, use that time to connect.

Even if you’re in different parts of the world, take a few moments in the evening to check in with one another emotionally. They say that absence makes the heart grow fonder, and perhaps there's something to the old cliche, but it's so much nicer to stay connected from afar. Facetime is a beautiful invention, but regular phone calls and texts throughout the day are nice too.

Ask one another the following questions each night before bed.

  1. Is there anything on your heart you want to talk about?
  2. Did I do anything today that upset you?
  3. What was your highlight and lowlight of today?
  4. Are you looking forward to and/or dreading anything about tomorrow?
  5. What do you need from me to make tomorrow a good day?

Time is our most valuable resource. It’s finite and we never know how much of it we have left. How do you want to spend it? If falling in love and building a partnership is important to you, then you have to make time for a relationship in your world.

The good news is, with Executive Matchmakers, we take most of the time-consuming work out of dating. You don’t have to weed through dating apps or attend every (un)Happy Hour in town. We introduce you directly to exceptional, like-minded, relationship-ready women


a couple looking adoringly at one another. they should use the three month rule to evaluate their relationship potential soon.

The Three Month Rule: What It Is and Why It Matters

When you start dating someone new, every moment can feel exciting and full of possibilities. But as the initial butterflies begin to settle, you might find yourself wondering, "Is this relationship going anywhere?" Enter the three-month rule—a widely recognized guideline in the world of romance that suggests the first three months of a relationship are crucial for determining its future. In this blog post, we'll explore the three-month rule in depth, talk about why it matters, and illustrate how you can use it in your romantic relationships.

What Is the Three-Month Rule?

The three-month rule is a timeframe that many people in the dating world use to evaluate the potential of a new relationship. It suggests that within the first three months, you should have enough information and experience with your partner to decide whether you want to continue the relationship or move on. This period allows you to get past the initial infatuation and see each other more clearly, both the good and the not-so-good aspects.

Why Three Months?

Three months is often considered the sweet spot because it's long enough to get to know someone beyond the surface level but not so long that you waste time if the relationship isn't right for you. Here's why this timeframe works well:

Getting Comfortable

In the beginning, the excitement of a new relationship can overshadow everything else. You're getting to know each other, sharing firsts, and the novelty makes every moment thrilling. This phase, often called the "honeymoon period," is characterized by a surge of feel-good hormones like dopamine and oxytocin. These chemicals can make everything seem perfect, glossing over potential issues.

After about three months, these intense feelings start to stabilize. You and your partner begin to relax and show more of your true selves. This is crucial because long-term relationships are built on authenticity and comfort, not just excitement. By three months, you’re likely to see each other in a variety of situations—both good and bad—which gives a more accurate picture of compatibility.

Routine and Reality

The first few dates are often carefully planned, exciting, and somewhat idealized. However, as time goes on, you start to settle into more of a routine. You might spend more time doing everyday activities together—cooking dinner, running errands, or just hanging out at home.

These ordinary moments are important because they reveal how you and your partner function in a typical day-to-day setting. You get to see how they handle stress, their habits, their reactions to minor inconveniences, and their general demeanor when they're not trying to impress you. By the end of three months, you should have a pretty good idea of how they fit into your life and vice versa.

Red Flags and Green Flags

Three months provide enough time to identify both red and green flags in your relationship. Red flags are warning signs that something might be off, such as consistent dishonesty, disrespect, or incompatible life goals. Green flags, on the other hand, are positive indicators like kindness, reliability, and shared values.

Early in a relationship, it’s easy to overlook red flags because of the initial attraction and desire to make things work. However, as time progresses, these issues can become more apparent. For example, you might notice patterns in how your partner handles disagreements, how they treat others, or how they manage their responsibilities. Identifying these flags helps you make an informed decision about whether to continue the relationship.

What to Look for in the First Three Months

The first three months can’t tell you everything about how a relationship might work out, but there are some signs to look for. Having important similarities or differences in the following areas can help you judge your overall compatibility moving forward.

  • Communication Style: How well do you and your partner communicate? Good communication is the cornerstone of a healthy relationship. Pay attention to how your partner expresses their feelings, handles conflicts, and listens to you. Are they open and honest? Do they respect your opinions and feelings?
  • Shared Values and Goals: Are your values and life goals aligned? While you don't need to agree on everything, having similar values and goals can make a relationship smoother and more fulfilling. Discuss topics like family, career aspirations, and lifestyle preferences to see if you're on the same page.
  • Consistency and Reliability: Is your partner consistent in their behavior and reliable? Trust is built on consistency. Notice if they follow through on their promises and if their actions match their words. Reliability is a key indicator of a partner's commitment and respect.
  • Emotional Support: Does your partner provide emotional support? A healthy relationship involves being there for each other during both good and bad times. Assess if your partner is empathetic and supportive when you need them.
  • Fun and Enjoyment: Do you enjoy spending time together? Having fun and enjoying each other's company is essential. Whether it's shared hobbies, humor, or simply feeling comfortable around each other, mutual enjoyment strengthens your bond.

Making the Decision

As you approach the three-month mark, take some time to reflect on your relationship. Consider these questions:

  • Do I feel happy and content with my partner?
  • Do we communicate well and resolve conflicts healthily?
  • Do we share similar values and goals?
  • Is my partner consistent and reliable?
  • Do we support each other emotionally?
  • Do we genuinely enjoy our time together?

If your answers are mostly positive, your relationship has strong potential. However, if you find yourself doubting or feeling unhappy, it might be time to reconsider.

Tips for Navigating the Three-Month Mark

The decision to get serious in a relationship can be a nerve wracking one, no matter what you choose to do ultimately. Here are a few tips for getting through this transitional period:

Have an Honest Conversation: Discuss your feelings and thoughts with your partner. An open and honest conversation can help clarify where you both stand and what you want moving forward.

Trust Your Instincts: Listen to your gut feelings. If something feels off or you're not as invested as you'd like to be, it's okay to acknowledge that.

Be Patient and Kind: Remember, every relationship is unique. Be patient with yourself and your partner as you navigate this timeframe. Kindness and understanding go a long way.

Don’t Rush Decisions: While the three-month rule is a helpful guideline, it's not a strict deadline. If you need more time to make a decision, that's perfectly fine. The goal is to build a healthy and fulfilling relationship, not to meet an arbitrary timeline.

Final Thoughts

The three-month rule is popular in the dating world for good reasons. It provides a balanced timeframe to move past initial infatuation and start seeing the real dynamics of a relationship. However, this check-in occurs early enough in your relationship that you haven't had time to get too serious yet. By focusing on shared values, consistency, and trusting your gut in the first three months, you can make a well-informed decision about your relationship's future.


a man and woman looking at their phones and smiling from two different locations. they are talking about their long distance date ideas.

Long-Distance Date Ideas

Being in a long-distance relationship can be challenging, but it also offers a unique opportunity to get creative with how you spend time together. While you may not be able to hold hands or share a meal at the same table, there are countless ways to stay connected and keep the romance alive from miles apart. Whether you're new to long-distance dating or a seasoned pro looking for fresh ideas, this post is packed with date ideas to help bridge the gap between you.

Tips for Creating Connection When You're Long Distance

Maintaining a strong connection in a long-distance relationship can be challenging, but it is certainly achievable with effort and creativity. Read on for some valuable tips for creating meaningful moments of connection, no matter how far apart you are.

  • Surprise Each Other: Send unexpected gifts, handwritten letters, or even a surprise food delivery. These small gestures show that you’re thinking of each other.
  • Create Traditions: Establish little rituals that are unique to your relationship, like a weekly movie night or a daily good morning text. These traditions create a sense of continuity and shared experience.
  • Be Honest and Open: Share your feelings and thoughts openly. Being transparent about your emotions can help you develop a sense of trust and understanding. Consistent and open communication allows you to give and receive emotional support from a distance.
  • Use Technology: Leverage technology to feel closer. Send each other flirty texts throughout the day. Set up a regular schedule for video calls or to spend time together doing something else virtually. Apps for video chats, synchronized movie nights,, and even online games can make the distance feel shorter.
  • Plan Visits: Whenever possible, plan visits to see each other. Having a countdown to your next meeting can boost your spirits and give you something to look forward to.
  • Talk About the Future: Discuss your future plans and goals. If possible, have a plan for your lives and careers to eventually bring you to the same place. Focus on the positives of your relationship as much as possible. Remind each other why you’re together and the strength of your bond, even when things get tough. This reinforces your commitment to each other and helps you stay focused on your shared dreams.

Long Distance Dates

Being in a long-distance relationship can be tough, but it also gives you a chance to get creative. Ask your partner out on a date. It's important to make time for one another, even when you're separated by distance. Whether you’re miles apart for a few months or navigating a longer stretch, here are some fun and engaging date ideas to help you feel closer, no matter the distance.

1. Synchronize Your Movie Night

Who says you need to be in the same room to enjoy a movie together? Apps like Teleparty allow you to synchronize your watching experience between two or more screens. Pick a movie, grab some snacks, and hit play at the same time. Use video chat to share your reactions and discuss your favorite scenes. For added fun, make it a theme night with matching snacks or costumes based on the movie you’re watching.

2. Cook the Same Meal

Cooking can be a delightful and intimate experience, even from afar. Choose a recipe you both like, gather the ingredients, and cook together via video call. Compare your final dishes and enjoy a virtual dinner date. This way, you can share the experience of making and eating a meal together.

3. Play Online Games Together

If you’re both into gaming, there are plenty of online multiplayer games you can play together. From cooperative games to competitive ones, find something you both enjoy. If gaming isn’t your thing, try solving online puzzles or escape rooms together. It’s a great way to team up and have fun.

4. Virtual Tours and Museum Visits

Explore new places together without leaving your home. Google Arts & Culture allows you to virtually explore the collections of some of the world's most renowned museums. Many museums and landmarks also offer their own virtual tours. Pick a location, take the tour, and discuss what you see. You could explore the Louvre, the Smithsonian, or even take a virtual walk through a foreign city.

5. Book Club for Two

If you both love reading, start a mini book club. Choose a book to read at the same time and set dates to discuss different sections. This gives you something to look forward to and provides plenty of conversation topics. Plus, you can learn more about each other’s tastes and thoughts.

6. DIY Art Projects

Get artsy with a virtual craft night. Pick a project you both can do, like painting, drawing, or even digital art. Share your progress and final pieces over video chat. Not only is it a fun way to spend time, but you also get a keepsake from the date.

7. Plan Your Future Adventures

Use this time to plan future trips and activities you want to do together. Create a shared document or a vision board with ideas, pictures, and notes. It gives you both something to look forward to and shows that you’re committed to your future together.

8. Trivia and Quiz Nights

Challenge each other with trivia questions or take online quizzes together. You can find quizzes on just about any topic, from movies and music to history and science. It’s a fun way to test your knowledge and learn new things.

9. Virtual Stargazing

If you both enjoy astronomy, plan a night to look at the stars. Use an app to identify constellations and share what you see through video chat. You could even create a stargazing playlist to listen to while you enjoy the night sky together.

10. Exercise Together

Stay active by doing a workout together. Whether it’s yoga, a dance class, or a simple workout routine, it’s a great way to stay connected and healthy. Encourage each other and maybe even set some fitness goals together.

A Little Effort Goes a Long Way

Long-distance relationships come with their own set of challenges, but with a little creativity, you can make the distance feel a lot shorter. Try out these date ideas and tips to keep the romance and fun alive. The effort you put into staying connected will only make your relationship stronger.


Why Are Executives Drawn to Matchmaking?

In the bustling world of business, executives face countless challenges daily. From managing teams to closing deals, the pressure is immense. But amidst all this chaos, there's one area where many high-ranking professionals are seeking a helping hand: their romantic lives.

Matchmaking is an age-old practice that’s becoming increasingly popular among executives. But why are so many leaders turning to professional matchmakers?

The Unique Challenges Executives Face

Being an executive isn't just a job—it's a lifestyle. These high-powered individuals have packed schedules that often demand their attention from dawn till dusk. For many, this leaves little room for personal pursuits, including dating. These are a few of the unique challenges executives face in their search for love.

Limited Free Time: Executives are constantly on the go. Their days are filled with back-to-back meetings, strategy sessions, and business trips. By the end of the day, there's often no energy left for social activities, let alone the time-consuming process of dating. Finding the time to meet new people, go on dates, and nurture a relationship can seem almost impossible.

High Expectations: Even when executives carve out time for dating, the traditional dating scene often doesn't fit their lifestyle or expectations. Long hours and unpredictable schedules can make it difficult to commit to regular dates. In addition, typical casual dating activities like mini golf or ice cream dates might not appeal to someone with more sophisticated tastes.

Privacy Concerns: For high-profile executives, privacy is paramount. Using dating apps or attending casual meet-ups can feel too public. There’s always the fear that their personal lives could become news, potentially impacting their professional image and responsibilities. The idea of their dating escapades becoming office gossip or, worse, making headlines, is a major deterrent.

What Makes Matchmaking So Appealing?

For many executives, enlisting the help of a matchmaker is more than just a personal choice—it’s a strategic decision.

The dating scene can be stressful and time-consuming. We alleviate this burden by handling the initial stages of dating, from introductions to planning dates, reducing the overall stress for busy executives.
Lindsay Mills, Director of Matchmaking

Here’s why investing in a matchmaking service can be incredibly beneficial:

  • Time Efficiency: Matchmakers do the legwork, screening potential partners based on the client’s preferences and values. This means you only meet people who are truly compatible, saving you time and energy.
  • Personalization: Unlike algorithms on dating apps, matchmakers provide a human touch. They get to know their clients personally, understanding their lifestyle, goals, and what they’re truly looking for in a partner.
  • Quality Over Quantity: When you work with a matchmaker, you won’t waste every Saturday on a first date that goes nowhere. Instead, you’ll get to skip the awkward dinners and only meet potential partners who are worth your time.
  • Privacy and Discretion: For many executives, privacy is paramount. Matchmaking services offer a confidential way to date, ensuring that personal details remain secure and away from the public eye.
  • Expertise and Guidance: Matchmakers are professionals who specialize in relationships. They offer valuable insights, advice, and support throughout the dating process, helping executives navigate the complexities of finding a meaningful connection.

The Modern Matchmaking Experience

In today's fast-paced world, finding the right partner can be challenging, especially for busy executives. Matchmakers are not just about setting up dates. They take a meticulous approach to find the perfect match for their clients. Modern matchmakers use a blend of science, intuition, and personalized attention to help their clients find love.

Here’s how they do it:

Many matchmakers start with comprehensive personality assessments. This is a tool that helps both matchmakers and clients to gain a clear understanding of what kind of partner would best suit the client’s needs.

These tests help identify the traits, values, and preferences that are most important to their clients. By understanding these core aspects, matchmakers can pinpoint compatible partners. This also starts off an ongoing conversation between the client and matchmaker that will continue throughout the matchmaking journey.

To get a deeper sense of their clients’ needs and desires, matchmakers often also conduct detailed interviews. This one-on-one time allows matchmakers to gather insights into clients' past relationships, future goals, and what they truly seek in a partner.

Beyond assessments and interviews, experienced matchmakers rely on their intuition and expertise. They consider the nuances of personality and chemistry that can’t be captured on paper. Their personal touch helps in making more meaningful and successful matches.

Support Beyond Matching

Matchmaking services often extend beyond just finding a match. Many offer additional support to ensure their clients are not only ready to meet the right person but also prepared to maintain a healthy relationship.

I'm definitely an emotional support person for my clients. As matchmakers, we provide more than logistical assistance. We’re a safe space for executives to express their vulnerabilities and receive constructive feedback on their dating experiences.
Lindsay Mills, Director of Matchmaking

A matchmaker can help your date go off without a hitch. It's hard enough to date without a packed schedule and a high-pressure career. The extra support matchmakers offer to executives helps them to not only meet potential partners, but to make a great first impression as well. Here are some of the ways matchmakers help their clients beyond making introductions:

  • Dating Skills Improvement: Matchmakers provide guidance on how to navigate the dating world, offering tips on communication, etiquette, and building connections.
  • Confidence Building: They help clients boost their self-esteem and approach dating with a positive mindset, making them more attractive and open to potential partners.
  • Relationship Readiness: Coaching ensures that clients are emotionally and mentally prepared to invest in a relationship, fostering long-term success.
  • Concierge Service: Matchmakers are not only invaluable resources for helping you navigate a date successfully, they can plan it for you too! A matchmaker can make restaurant reservations and other essential plans for your date beforehand to ensure everything goes smoothly without you lifting a finger.

In the fast-paced world of business, finding love can often take a backseat. However, with the rise of professional matchmaking services, executives no longer have to choose between a successful career and a fulfilling personal life. By turning to matchmakers, they can efficiently and discreetly find meaningful connections, ensuring that their hearts are as fulfilled as their resumes.


Six Strategies to Handle Awkward Silence on a Date

Do you find yourself loathing the dreadful "awkward silence" that accompanies some first dates? Between nervousness and the pressure to keep the conversation flowing, these painful pauses between two new people can feel pretty uncomfortable.

Navigating awkward silence on a date can be challenging, but with the conversation tools, you can keep the conversation flowing smoothly and maintain a comfortable atmosphere. Here are six strategies to help you handle those moments of silence:

Opt for Open-Ended Questions

It’s pretty much always great advice to ask questions on a date, but the type of question matters. If you want to keep the conversation going, ask your date questions that encourage them to talk.

Try to think of questions that might prompt your date to tell a story or give their opinion about something. By asking open-ended questions, you’ll encourage your date to share more about themselves.

If you want to keep the conversation going, ask your date questions that encourage them to talk.

Instead of asking questions like "Do you like hiking?" which can be answered with a simple "yes" or "no," frame your questions in a way that invites your date to elaborate. For example, you could ask, "What do you like most about hiking?" or “How did you get into hiking?” Asking in this way encourages your date to share their thoughts and experiences, leading to a more engaging conversation.

Share Personal Stories

Sharing personal stories or anecdotes can help break the silence and create a connection between you and your date. Share a funny or interesting story from your own life that relates to the topic you've been discussing.

For example, if you’ve been chatting about your favorite childhood movies, you could share a story of how you reenacted the scenes with your friends. A fun anecdote of your own can also encourage our date to take a trip down memory lane and share a story about their life in return.

Sharing your own lighthearted anecdote can encourage your date to open up with their own stories.

Be careful not to overshare too early in your dating relationship. Sharing too much too fast might make your date uncomfortable and sabotage your chances of connecting with one another. It’s okay—and encouraged—to get personal, but it’s also best to keep it lighthearted.

Play a Game

Injecting a bit of fun and playfulness into your date can turn an ordinary evening into a night to remember. Consider starting off with a lighthearted game or activity that sets the tone for laughter and bonding.

For instance, "Two Truths and a Lie" can be a fantastic icebreaker. It's a chance for you and your date to learn more about each other in a playful way. You'll share three statements about yourselves: two of them true and one a lie. As you take turns guessing which statement is the lie, you'll have a chance to tell fun stories and deepen your connection.

Another option is to play "Would You Rather." This game offers a delightful opportunity to explore each other's preferences and quirks. Would you rather spend a day exploring a bustling city or relaxing on a remote beach? Would you rather have the ability to time travel or read minds? These questions can lead to intriguing conversations and provide insight into your date's personality.

Icebreaker games like "Two Truths and a Lie" or "Would You Rather?" can help you avoid awkward silence by adding some structure to the conversation.

As always, keep it light. Try to steer clear of heavier topics like money, politics, and medical issues for now. The goal is to create a relaxed and enjoyable atmosphere where you can both let your guards down and be yourselves. It's a chance to share laughs, make memories, and strengthen your connection.

Talk About Your Surroundings

Use your surroundings as conversation starters. Imagine you're at a cozy cafe with your date. You could start by remarking on the charming decor – perhaps the vintage posters on the walls or the soothing color scheme. This opens up opportunities to ask questions like, "Do you have a favorite type of ambiance when you go out for coffee?" or "What's the most unique cafe you've ever been to?"

If you're at a restaurant, take note of the menu options. You might comment on the variety of dishes available or the chef's special for the evening. This could lead to discussions about food preferences, favorite cuisines, or memorable dining experiences. Ask your date about their favorite dish or what they like to cook at home.

Talking about what's happening around you can help you and your date stay in the moment.

Talking with your date about the things going on around you not only keeps the conversation flowing but also shows that you're interested in sharing the experience with them. Plus, it can create a comfortable atmosphere where both of you feel more at ease expressing yourselves in the moment.

Express Genuine Interest

When you're on a date, what's more appealing than someone who is truly interested in what you have to say, who actively engages with your thoughts and experiences, and who listens with intent rather than just waiting for their turn to speak?

Showing genuine interest in your date's thoughts, opinions, and experiences is not just a nicety; it's the only real way to form a connection. It's about more than just nodding along politely—it's about actively engaging with what they're saying, asking insightful questions, and showing that you value their perspective.

Active listening is key here. That means giving your date your full attention, making eye contact, and really focusing on what they're saying rather than letting your mind wander. Resist the urge to interrupt or interject with your own thoughts; instead, give them space to express themselves fully.

Showing genuine interest in your date's thoughts, opinions, and experiences is not just a nicety; it's the only real way to form a connection.

Asking follow-up questions is another crucial aspect of showing genuine interest. This demonstrates that you're not just passively listening, but actively engaging with what they're saying and trying to understand them better.

Expect Some Silence

Awkward silence can sometimes sneak up on us during a date. You know, when the conversation hits a lull, and suddenly you're both just sitting there, not sure what to say next. It's a moment that can make even the most confident person feel a little uneasy.

But “awkward” silence isn't always a bad thing. In fact, it can be quite natural and even a sign of comfort between two people. When you're truly comfortable with someone, you don't always feel the need to fill every moment with chatter. Sometimes, just being together in silence can be enough.

So, next time you find yourself in the midst of an awkward silence, take a deep breath and relax. Instead of scrambling to come up with something to say, try to embrace the moment for what it is. Maybe take the opportunity for some quiet reflection or simply enjoy each other's company without the pressure of constant conversation.

 Quiet moments are natural and can be a sign of comfort between two people.

When you're on a date with someone new, don't worry about a little bit of a lull in conversation. By incorporating these strategies into your dates, you can navigate awkward silence with confidence and ensure that both you and your date have a positive and enjoyable experience.


a person's hands as they hold their phone wondering if raya and other luxury dating apps are worth it

Is Raya Worth It? A Review of Luxury Dating Apps

Finding someone can be hard, and any tool that can help you navigate the murky waters of the dating scene is welcome, right? There are endless apps and sites aimed at singles who are looking for someone special.

The most popular services are mass-market dating apps like Bumble and Tinder, but there are more exclusive options for high-end clientele. But what if—just like their free and low-cost counterparts—these luxury platforms are more headache than they’re worth?

Why Users Are Leaving Apps

It’s no surprise that the issues plaguing dating apps exist pretty much across the board. The market is dominated by Bumble and Match Group, the company that owns Hinge, Tinder, OKCupid, and several other platforms. Most of these apps share a similar swipe-to-match format, making the user experience largely indistinguishable.

This popular format heavily features users’ photos. This is part of why dating apps foster a very appearance-focused environment, making it harder for users to feel comfortable as they look for connections. As one person tells The Guardian, “The apps are algorithmic doom barrels.

“It does not matter how handsome or beautiful or charming you are, there is this underlying tension that you are 10 swipes away from a person that outranks you on the conventional beauty and charisma scale. It’s enough to make you feel all the insecurities that you haven’t needed to swallow since you were a teenager and a whole realm of new adult ones.”
Dating App User, 29

This is far from the only issue with the apps’ designs. A lawsuit was brought against Match Group claiming that the company’s apps are designed to be addictive. Experts have found that dating apps light up the same areas of the brain as slot machines and addictive substances.

Despite apps’ gamification strategies, it appears that users are actually leaving once-popular platforms en masse. Despite plans for new features and specialty services, the apps are still struggling.

According to the New York Times, this is because users, especially young people, are looking to social media for online connections. Users are also less willing to pay for premium features that don’t yield premium results.

Are Luxury Dating Apps Better?

The services designed to be luxury experiences really aren’t all that different. Unfortunately, it can be difficult to determine at a glance which services are designed for relationship-minded singles.

Many platforms cater instead to sugar dating, semi-transactional relationships in which one partner receives gifts and/or a financial allowance in exchange for their romantic companionship. These relationships are typically between a younger and older partner, most commonly an older man and younger woman.

While there are plenty of scammy sugar dating sites to sift through, you’ll find few legitimate options. When it comes to the app market, there are a few to choose from, all with their own pros and cons. These are some that we discovered:

Luxy

Luxy is an app that offers bespoke matches based on exclusivity. Getting onto the platform is a feat in itself, with more than three-fourths of applicants being turned away during the 24-hour review period. Verified millionaires and those who pay to use the app can skip this waiting period.

Luxy’s acceptance criteria include “soft factors” like occupation, education, and profile photos. This ensures exclusivity, but it also means that tons of eligible applicants are never seen by others on the app. Many people attain a highly successful lifestyle through nontraditional paths, and these people will find it harder to qualify for Luxy.

One interesting thing about Luxy is that it very explicitly bans “sugar dating”. The app positions itself as a place for millionaires to meet millionaires. However, the app’s income verification is optional, making it difficult to ensure that only the top 1% of singles are present on the app. ID verification is done using an AI-powered software.

Pros
  • Exclusive membership pool
  • Sugar dating is banned.
Cons
  • Low acceptance rate
  • AI used for ID verification.
  • Income verification is optional.
  • Paying members can skip the 24-hour verification period.

Raya

Raya is one of the most exclusive online dating platforms operating today. For starters, you can’t just apply to join. First, a current Raya member has to refer you, then you’ll be invited to apply for membership. After that, you’ll be invited to join if your application is accepted.

While you don’t have to be a celebrity to make the cut, it certainly helps. The app, meant for creative professionals, requires its users to hand over their Instagram account as part of the application process.

While the company hasn’t published any specific requirements, it’s rumored that users need a minimum number of followers. Of the people who follow you, there need to be enough current Raya members present to seal the deal.

Once you make it onto the app, it’s a lot like the swipe-left, swipe-right format of other popular dating apps. Profiles are photo-centric, and writing a bio is optional. Raya does require an Instagram handle, providing users a small glimpse of their potential matches off the app.

Pros
  • Truly exclusive
  • Membership of high-level professionals
  • Celebrity-spotting
  • Instagram handles provide more information about other users.
Cons
  • Only for creative industries
  • Invasive sign-up process
  • Need to have Raya members in your Instagram follower list.
  • User experience is similar to other dating apps.

The League

When you join The League, it can go a few different ways. Most people download the app and join the waitlist, which can take a few months. Other lucky users can skip the line by paying for a membership or being referred by a friend on the app.

It’s worth noting that The League is owned by Match Group, the company currently under fire for its apps addictive features. While there are features of the app that are unique to The League, the basic concept is quite similar to the typical swiping format.

The main difference is the number of profiles you’ll see. Members of the free version of The League are only shown three potential matches per day, while the highest tier of membership, which costs hundreds of dollars per week, affords users seven profiles to peruse each day.

The information on all these profiles is taken from users’ LinkedIn profiles, which are manually screened by reviewers to determine eligibility. Once your profile is reviewed, you’ll be admitted to The League if you live in one of the cities they’re located in.

Pros
  • Exclusive membership
  • In-person events
  • Members are all vetted.
Cons
  • You’ll need to update your LinkedIn to apply.
  • Paid features are expensive and don’t offer much more than the free version.
  • Match Group has been sued for addictive app features.

All in all, it seems like luxury sites and apps are just as hit-or-miss as their mass-market counterparts, just with a higher price tag. If you’re looking for true luxury dating experience, look no further than a skilled matchmaker.

What We Offer

At Executive Matchmakers, we provide something more than just a database of members to endlessly sift through. We provide stellar introductions with eligible potential partners.

Private: We understand the sensitive nature of working with a matchmaker, which is why your membership will be kept private. We don’t post your profile, name, or photos, so you can join with the peace of mind that only a professional matchmaker can offer.

Personalized: There are no generic profiles or sifting through members. With Executive Matchmakers, you can date your way. Using our Signature Match process, we tailor your search to your unique personal preferences.

Commitment-Minded: Our service is designed for those who are ready to get off the dating treadmill and into a happy, fulfilling, long-term relationship. For successful singles who aren’t willing to compromise on quality, there’s no better choice than Executive Matchmakers.