Conversation

30 Questions to Get the Conversation Going

In her book, Captivate: The Science of Succeeding with People, Vanessa Van Edwards, separates conversation into three categories based on how long you’ve spent with someone: five minutes, five hours, or five days.

I believe everyone opens up at their own pace, so I categorize interactions into small talk, ice breakers, and connection builders with each one digging a little deeper to get to know the other person better.

Below, I’ve compiled ten sample questions for each section. 

Conversation is a delicate dance of leading and following. It’s a matter of giving and receiving information. There’s an art to being vulnerable and asking probing questions without crossing a boundary or oversharing.

If you’re going to ask about deal breakers, be cautious in how you do so. You don’t want to give off negative energy.

For example, don’t ask your date who she voted for or to which political party she subscribes. At the same time, don’t announce those things about yourself. It’s too direct and very off-putting. Instead, focus on sharing your core values and learning about hers.

If your values align, the rest will follow. 

Start Small

If you’re an introvert like me, small talk probably isn’t your area of expertise. Unfortunately, it’s a highly-valued social skill in our society. So, I find it helpful to have a few open-ended questions on hand, to get the other person talking and let them dominate the conversation.

This allows me and my anxiety a break so I can do what I do best—listen. 

  1. Have you read anything interesting lately?
  2. Do you belong to any organizations?
  3. Who is your celebrity crush?
  4. What is an average day like for you?
  5. Do you do any volunteerism or charitable work?
  6. What is your favorite/dream travel destination?
  7. Tell me about the best and worst parts of your day.
  8. When you visit your hometown, what is the one place you have to stop at?
  9. Do you have any pet peeves?
  10. What does your ideal weekend look like?

Small talk doesn’t have to be meaningless chatter about the weather. You can use it to really get to know someone on a deeper level if you ask purpose-driven questions and practice active listening.

For instance, by asking someone how they would spend their ideal weekend, you can discern things like:

  • Are they a morning person or a night person?
  • Do they prefer their alone time or group settings?
  • Are they an introvert or an extrovert?
  • What are their hobbies?
  • How do they like to spend their free time?

That doesn’t even include all of the inferences you can make from their non-verbal communication. And you didn’t have to barrage them with rapid fire questions. Also, be prepared to answer any question you ask in return.

Ice Breakers

I would advise you to limit yourself to one or two of these types of questions per date. They can range anywhere from whimsical to philanthropic, but one common thread is that they’re complex questions that require critical thinking.

These are those bizarre questions you see on interview lists like—What animal most closely describes your personality?

One question is fun, two is deep, three is just plain exhausting. They’re great questions, but like many great things, require moderation to be most enjoyable. 

  1. What skill or talent have you always wanted to master?
  2. Who is the most fascinating person you’ve ever met?
  3. Would you rather have the ability to speak any language or speak to animals?
  4. If you could pick a superpower, what would it be?
  5. Would you rather take several weekend getaways or one extravagant vacation?
  6. What do you do that other people think is annoying?
  7. Do you have any guilty pleasures?
  8. What is your most irrational fear?
  9. If you could solve one global crisis what would it be?
  10. What is the best gift you’ve ever given or received?

Connection Builders

These are deeper questions that can help you really get to know your date on a more intimate-level.

  1. What is your favorite book of all time?
  2. Tell me about your best friend.
  3. What do you want to accomplish in your lifetime?
  4. Are you close with your family?
  5. What do you love most about your work?
  6. Do you have any side-hustles or passion projects?
  7. How do you want your legacy to be remembered?
  8. What is the one thing that will put you in a good mood, no matter what?
  9. Who is the most influential person in your life?
  10. What is your primary Love Language?

Use your best judgement: if it’s your first date and you’re really hitting it off, these are pretty safe topics. However, if she’s not keen to open up, if her body language is closed off, if she’s giving you short answers—my advice is to stick to lighter topics of conversation until she’s more comfortable.

If your date is slow to open up in conversation, don’t write her off or hold that against her. You never know what she’s experienced in her past. Putting yourself back out there can be difficult. Again, if you share similar values, it’s likely a good match. Just be patient and give it time. 


Womens Intuition

The Science Behind Women’s Intuition

In honor of International Women’s Day, we’re going to take a look into the science of an age old phenomenon—women’s intuition.

Even the CIA knows women make better spies.

Okay, ladies, now let’s get in formation.

The British Journal of Psychology defined intuition as: what happens when the brain draws on past experiences and external cues to make a decision—but it happens so fast that the reaction is at an unconscious level.

Another definition is our brain’s ability to draw on internal and external cues while making rapid, in-the-moment decisions. Often occurring subconsciously, intuition relies on our brain’s ability to instantaneously evaluate the situation and make a decision based on gut-instincts.

Judith Orloff, MD, is the assistant clinical professor of psychiatry at UCLA and the author of Guide to Intuitive Healing: Five Steps to Physical, Emotional, and Sexual Wellness. She said the following:

Just like the brain, there are neurotransmitters in the gut that can respond to environmental stimuli and emotions in the now—it's not just about past experiences. When those neurotransmitters fire, you may feel the sensation of butterflies or uneasiness in your stomach. Researchers theorize that gut-instinct plays a large role in intuition by sending signals to your brain. I teach my patients to always listen to their gut—that sixth sense that's telling you something might not be right—particularly if you're sensing danger. If you listen to it and you're wrong, you've lost nothing. Perhaps you took a longer route home or you ducked into a store until the feeling passed. If you don't listen to it and you're right, things could turn out very badly. More often than not, your gut is right, so listen up! It's always better to be safe than sorry.

Science suggests women's intuition is a product of evolution. Females with a strong ability to understand and predict the needs of their offspring and mates thrive over females with inferior senses.

Previous generations were often expected to be seen but not heard. Because of this, they developed a deep sense of observation by becoming hyper-sensitive to the feelings and nonverbal cues of others.

Women may exhibit more intuition, empathy, collaboration, self-control, and appropriate concern because of increased blood flow in the brain. Or as Dr. Daniel Amen, Founder of the Amen Clinics, put it:

“The female brain is wired for leadership.”

Perhaps they should have been listening to us all along.

We are also better at showing our emotions through facial expressions, tone of voice, and body language. Whereas, men are better at hiding their emotions and maintaining a poker face.

But often, we’re still able to decode your tells. 

Research on nonverbal communication skills shows women are better at reading facial expressions and emotions. As a result, we are more likely to pick up on the subconscious cues of others.

The University of Cambridge conducted an experiment by showing people pictures of eyes. The subjects were then asked to conclude the person’s mood based on the appearance of the eyes in the photo.

Unsurprisingly, the ladies dominated.

When comparing MRI scans of brain activity, the female brain reveals an increased number of neural connections. This makes it more efficient and helps with interpreting one’s social surroundings.

On the other hand, the male brain is neurologically wired to be more logical, making it more effective at linking perception with action. This helps men be more intuitive. You guys also have better spatial intelligence, so stop making us navigate!

History and science both agree women’s intuition is more than just a myth. Listen to that little voice in your head; trust your gut. It might just save you a lot of heartbreak.


Worst Dating Advice

World’s Worst Dating Advice

Rules are meant to be broken. It’s a new decade, so take the worst dating advice you’ve been told throughout the years erase it from your memory.

There is an entire genre of self-help books dedicated to dating advice, much of which is solid, data-based research, but an equal amount is opinion-based and anecdotal. As they say, don’t believe everything you read. 

Love is Magical

Soulmates, twin flames, love at first sight, happily ever after—these are the types of magical love we strive for from our very first bedtime story. 

Real life love is much more practical. Don’t get me wrong, it has its magical moments when you swear the earth stops spinning. But true love, the kind that lasts forever, is a choice that must be made every single day.

Love is a verb as much as it is a noun.

The worst dating advice I ever heard was: If there is no chemistry on the first date, it’s not worth pursuing.

Attraction is not limited to our primal instincts, even though it may feel that way sometimes. As feelings of love and admiration develop, so does that magical, unexplainable spark.

Don’t write someone off right away. Some of our strongest matches have come from couples that we initially had to talk into going on a second date.

Keep Conversations Light

We’ve talked about the opposite end of this spectrum: oversharing. You don’t want to share too much too soon, but you also don’t want to avoid meaningful conversations that occur naturally. As the relationship progresses, you should feel comfortable opening up about more sensitive topics. This includes things like family goals, career dreams, and wishes for the future.

Imagine investing months into someone only to find out your goals for the future couldn’t be more opposite. You want to get married and raise a family, but she doesn’t want marriage or children.

By not defining the relationship and communicating your needs, you run the risk of wasting a lot of time dating people who aren’t a viable match. Executive Matchmakers helps weed out deal breakers so this doesn’t happen

Be Your Best Self

We’re taught to be on our best behavior in all new relationships, and it’s true—to an extent. On a first date, at a new job, or even with a budding friendship, it’s always important to put your best foot forward. 

As Miranda Lambert put it, Hide your crazy and start acting like a lady.

But there comes a time in every new relationship, where both parties have to be vulnerable, let their guard down, and show their flaws. If this doesn’t occur, the connection will remain in surface-level acquaintanceship territory rather than growing into something deeper.

Often in new relationships, people will behave how they think their partner wants them to behave. This leads to a myriad of problems.

If you’re not behaving as you normally would, your partner doesn’t truly get to know you. She may fall in love with a false version of you. This often leads her to a sense of feeling defrauded. And you’re left feeling as if your partner never truly knew you after all. 

In trying to be everything your partner wants, you may lose your sense of self.

Communicating one’s needs, expectations, and boundaries is key for building the foundation of any new relationship. 

You’re finishing up dessert on your third date, when your partner suggests a bar across town for a nightcap. You know you have an important meeting first thing in the morning, but you don’t want to upset her, so you say yes. Unfortunately, while you’re sharing a drink an hour later, the mood has shifted. You’re in your head, stressed out about the morning, and constantly checking your watch. Your date studies you closely for some sign of what caused the flip after dinner, but ultimately she’s left clueless.

If you had set boundaries and explained why you needed to go home after dessert, you could have both ended the night on a high note, excited for your next date. 

What is the absolute worst dating advice you’ve ever gotten? Just remember, not all advice is good advice! When in doubt, ask your Matchmaker


frustrated man

Professional Matchmaking: How to Never Get Ghosted Again

If you have spent any amount of time in the dating scene over the past few years, chances are you have heard of the ghosting phenomenon. Hopefully, you aren’t guilty of ghosting anyone, and likewise have not been the victim of a ghost. At Executive Matchmakers, our priority is helping you find genuine, lasting love, so you never get ghosted again.

Did you know that over half of today’s daters have first-hand experience with ghosting?

What exactly does it mean to get ghosted?

Ghosting is the sudden, unexpected cease of all communication from one party within a relationship. Although the term is new, it wasn’t born through dating apps, and it isn’t a new concept.

I assume you have heard the cliché of a father who went out for cigarettes and never came back—that guy ghosted his whole family. It’s not specific to romantic relationships either, we all know a guy who ditches his friends whenever he gets a girlfriend.

The most common form of ghosting can be explained by the following scenario:

You matched with a woman online and shared a number of pleasant chats. You ask for her number and eventually to meet in person. After a few dates and weeks of FaceTiming, she suddenly stops responding to your texts. She dodges your calls, and bails on your weekend plans. You assume she’s caught up in work and give it a week or so before you start to worry. Eventually, you ask her what went wrong, but you get no answer. You’re then left wondering if you did something wrong, she met someone else, or even if she died. 

This is an emotionally painful situation to find yourself in. You may have been the perfect gentleman and said all the right things, but she just didn’t see a future with you for one reason or another. Unfortunately, she was unable to communicate that to you—so she ghosted.

It’s really important to remember if someone ghosts you, that behavior says more about them than you. It’s about their discomfort.” -Dr. Jennice Vilhauer

Why do I keep getting ghosted?

I’m a firm believer that most negative behavior stems from a basis of fear. When humans are afraid, they respond with either fight, flight, or freeze. Ghosting is a combination of the latter two. The ghost freezes communication because she’s afraid of the outcome if the relationship continues, and she flees from the situation in order to avoid difficult conversations or unwanted outcomes.

Fear isn’t the only reason women ghost though. Maybe she’s busy with her career or her family. She could be going through a rough time, either mentally or physically. I think we can all agree, COVID-19 has thrown everyone into a bit of a crisis. Maybe she met someone unexpectedly or an ex came back into her life. And there’s the hardest pill of all to swallow: she’s just not that into you.

But what is she afraid of?

Perhaps it’s a fear of rejection. A sort of get them before they get me first approach. People with this method of dating are not in the right mindset for a long-lasting, committed relationship anyway. Someone who has a pattern of leaving before they get left, will never stay long enough to work through the hard stuff that life tends to throw at us.

One of the most common fears that cause women to ghost is the fear of retaliation. We have been socialized and trained to play nice and never offend a man’s ego. Because of that, some women were simply never taught a polite but effective way to turn down a man’s advances.

How many comedies play off of a woman’s inability to kindly reject a man who buys her a drink at a bar, when she’s clearly not interested in him? There is more truth in that than most of us would like to admit.

Unfortunately, there is a darker side to this fear of retaliation. And that is the very real threat of violence and abuse women have historically experienced at the hands of men with bruised pride.

If the woman who ghosted you has been a victim of or a witness to abuse in her lifetime, try not to take it personally. She probably has a level of fear that revolves around her interactions with men, and ghosting feels like a safer alternative.

Is she too busy or just lazy?

Honestly, does it matter? Whether she’s hustling in her career working 80-hour weeks, or has been on her couch in the same pair of sweatpants all weekend—the fact is she hasn’t made time for you in her life. She may be actively ignoring you, AKA ghosting, or she may just have a mile-long priority list that doesn’t include you.

Will one scenario sting less than the other? I doubt it. It hurts when someone you were developing feelings for doesn’t reciprocate, no matter what the circumstances are.

That being said, I’m a proponent of second chances. If she reaches out with an apology and a valid explanation for being absent, why not give it one more date? That is if you still see potential in the relationship, of course.

How do I never get ghosted again?

Well, there are no guarantees in life, but matchmaking is a smarter, safer way to meet people.

The use of dating apps has created a lot of lazy daters. We pick up our phones and sometimes getting a date is as easy as ordering a pizza. If we don’t catch the other person’s attention within a few messages, they get bored and move on to the next app. We have thousands of possible matches in our pocket. We may give it a few dates, and if that person doesn’t blow our mind, we start swiping again.

It’s all pretty indicative of where we are as a society in terms of instant gratification.

But there is good news! There are alternatives to the monotony of endless swiping, texting, and eventual ghosting. There are better, safer, more efficient ways to date in 2020. At Executive Matchmakers, we have years of experience matching like-minded singles who go on to happy, healthy, long-lasting relationships.

The main reason that ghosting is so prevalent in recent years, is because we’re meeting complete strangers at an unprecedented rate. Previous generations met their mates through mutual friends, family members, church, work, and school. They typically had at least one other person in common with their date. 

Take the following situation for example:

Let’s say your Aunt set you up with a young woman from her church. If you were rude on your first date, or you completely disappeared on the woman, it’s likely that she will complain to your Aunt about your behavior. Your Aunt would then hold you accountable and you would face consequences. 

When you date strangers from the internet with no mutual connections, there is little to no accountability, and people feel free to behave in ways they probably wouldn’t if their Aunt was privy to the situation.

People are less likely to ghost if there is an additional person they have to answer to...like a matchmaker.

Your personal matchmaker will not only work to match you with your ideal partner, but she will also follow up with you and your matches to provide her expert coaching and advice. Our priority is helping you find genuine, lasting love so you never get ghosted again.


Dating Screen

Executives - Think Outside the Dating Screen!

Matchmakers Are Your Dating Headhunters.

When we talk to potential new clients, a fair number admit that they never thought of hiring someone to help them with their love life until they stumble upon an article or ad for matchmaking. For many successful men and women, it just makes sense right away. Dating is a time investment in hopes of eventually finding a long-term relationship. Alternatively, the online dating screen often produces endless profile scrolling, bad matches, and requires a massive time investment.

Matchmakers are your dating efficiency, love life headhunters! We cut your time spent on dating screens down to zero. Instead of you spending hours scrolling through Tinder, Match, OkCupid, or others, we search our massive "Little Black Book" and use our Personal Scouts to find you high-quality dates. If you are still unsure about the benefits of hiring a matchmaker, keep reading. We'll explain why matchmaking services have the potential for a high ROI for those looking for real love.

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Oversharing

Oversharing - Too Much, Too Fast

Beware! The fine line between being authentic and oversharing

Andrew and Melissa's second date seemed to be going great. They were dining on the patio at one of Andrew's favorite local wineries. The sunset was spectacular and Andrew's anxiety about bringing a date to one of his favorite places was almost gone. Melissa seemed to get his dry humor and he appreciated her quick wit and warmth. She had even leaned into him when they were waiting to be seated and then held his hand when they walked to their table overlooking the vineyards below.

While they were sipping a spectacular Russian River Valley Pinot Noir, Melissa casually asked Andrew about his previous dating experience. Without thinking, Andrew launched into the FULL story of his last long-term relationship. Including all the details about their custody dispute over the puppy he had gotten his girlfriend for her birthday, and their disastrous last vacation. Andrew told her how they met, about their moving in together, all the things that went wrong afterward, and their messy breakup. When Andrew finally stopped talking, he noticed that Melissa was no longer smiling. After finishing dinner, Melissa got a Lyft home.

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