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.
- Have you read anything interesting lately?
- Do you belong to any organizations?
- Who is your celebrity crush?
- What is an average day like for you?
- Do you do any volunteerism or charitable work?
- What is your favorite/dream travel destination?
- Tell me about the best and worst parts of your day.
- When you visit your hometown, what is the one place you have to stop at?
- Do you have any pet peeves?
- 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.
- What skill or talent have you always wanted to master?
- Who is the most fascinating person you’ve ever met?
- Would you rather have the ability to speak any language or speak to animals?
- If you could pick a superpower, what would it be?
- Would you rather take several weekend getaways or one extravagant vacation?
- What do you do that other people think is annoying?
- Do you have any guilty pleasures?
- What is your most irrational fear?
- If you could solve one global crisis what would it be?
- 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.
- What is your favorite book of all time?
- Tell me about your best friend.
- What do you want to accomplish in your lifetime?
- Are you close with your family?
- What do you love most about your work?
- Do you have any side-hustles or passion projects?
- How do you want your legacy to be remembered?
- What is the one thing that will put you in a good mood, no matter what?
- Who is the most influential person in your life?
- 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.
Dating After Divorce: How to Prepare for a New Chapter
According to researchers, divorce is the second most stressful life event one can experience. Preceded only by the death of a loved one and followed by a health crisis. Dating after divorce can be equally stressful if you’re not prepared.
The first thing you should consider is how dating has evolved tremendously over the last decade. Tinder came on the scene in September 2012, followed by Bumble in 2014.
So, chances are things will be very different from first dates you’ve experienced in the past. Gone are the days of buying her flowers and picking her up at her front door for a first date.
When to Get Back Out There
Unfortunately, I cannot definitively say when someone is ready to start dating after divorce. Every relationship is different; every person is different. Only you will know when you’re ready; move at your own pace.
Your friends and family will encourage you to move on and play the field. They mean well, but you know yourself better than anyone else does. Trust your gut. It’s okay if you’re not ready.
You should wait until your marriage is officially over, including all the legalities: separation of assets, custody agreements, alimony, etc.
If you are emotionally over your ex, but the paperwork isn’t quite dry, I would advise you to just put off seriously considering another relationship for those last few months.
Things start to get messy when you start something new without tying up all of your loose ends first.
Secondly, ask yourself—is it really another relationship you want? Don’t fire up the dating apps just because you’re feeling a bit lonely on Sunday evening. Are you looking for validation in the form of shirtless bathroom selfies or are you truly ready to open your heart and life up to another person?
When a marriage dissolves, so does the dream of a life together. You planned forever with someone; imagined growing old with her. Then, suddenly it’s all gone. You have to take the time to mourn the loss, just as you would a death.
As painful as it is, let yourself experience the grief. Don’t try to mask it with new women—that will only delay your healing.
After about a year, most people feel ready to move on. But you should still expect some intense feelings to pop up from time to time. Trauma has a way of doing that. Allow yourself to have those mini meltdowns. It is a natural part of the healing process and it means you’re one step closer to dating after divorce.
Use this time alone to learn about yourself. Reflect on your failed marriage. Will you do anything differently next time? What characteristics will you look for when you’re ready to start dating after divorce?
What to Expect When You're Dating After Divorce
It’s normal to struggle with how to step out of the husband role and into the boyfriend position.
This woman has not made a commitment to you yet. You have not stood in front of God and your loved ones to say vows. You are not her husband.
Let me say that one more time—you are not her husband.
Maybe someday you will be her husband, but don’t rush it. Don’t force it. Relish your time as the boyfriend. Learn about yourself, your partner, and how you fit into one another’s lives. Use this time to see if she is someone you could spend forever with.
Don’t use intimacy to manipulate the situation. Some people use physical touch with multiple partners as a way to escape their emotions. Others combine sex and monogamy in an attempt to make the relationship progress more quickly.
Both usually end in disaster.
When you’re used to being one-half of a whole, it’s very difficult to learn how to be on your own. It’s a lonely process full of self-doubt.
There will be women who seem perfect for weeks and they will disappear out of thin air. This is called ghosting.
Try Something New
I would wager you learned a thing or two about yourself during your divorce that you didn’t know before. I challenge you to continue doing that. Expand your horizons. Try new things. Work on yourself. See a therapist. Start a new hobby.
Explore your deal breakers and really discern if they are things you need in a partner or just preferences you want. Go out with women you normally wouldn’t consider.
Give personality and common interest your primary attention, and make physical attraction a secondary criteria. Science has shown that attraction grows over time. Our brains release a cocktail of happy hormones whenever we are around people who make us laugh and feel good.
The more time you spend with that person, the better she looks.
You may find that you’re attracted to women who look nothing like your ex. Trauma has a way of doing that too.
Trust that if your Matchmaker suggests someone, there is a definitive reason that the two of you were paired. This is your chance to meet all different types of women from various backgrounds and cultures.
Give it a shot. I dare you.
Reflection: The First Step to a Great Life
We rarely take time out of our day-to-day lives to really dig deep and check in with ourselves. So, that’s exactly what I want you to do right now. Take a few deep breaths, and spend some time in reflection. Think about your life, decisions, relationships, triumphs and trials.
What life lessons helped shape the person you’ve become? What is most important to you as we move through this new decade? Do you have any hopes or dreams? Are there plans you can implement right now to start moving the needle in that direction? Is there a bad habit you need to quit? Do you want to fall in love? Get married? Start a family?
Reflection and Response
Change doesn’t come easily. In fact, it often goes against our very nature, but it’s a necessary part of life. After you’ve completed a thorough evaluation and reflection of your life thus far, it will be easier to make concrete plans for a better future.
What needs to fundamentally change for you to make room for love in your life? Maybe there’s an ex you need to let go of, or a heartbreak you haven’t fully healed from. Perhaps, 2020 just beat you down a few too many times.
COVID-19 has certainly been a worldwide wake up call. Life is short. Now is the time to be brave, bold, and confident enough to take those first steps. Your matchmaker can help you nurture the positives in your life and create a solid foundation for you to find love.
Make this Year Count
Step outside your comfort zone and make this year worthwhile. We only have so many trips around the sun, don’t you want to spend them living your dreams?
Do you have your eye on someone new? Is there a colleague you want to get to know better? Valentine’s Day is only a week away; gather the courage to send them a card or small gift.
If you’re in the early stages of a new relationship. you don’t want to overwhelm your partner by going all out before they’re ready. Open a dialogue, ask them what they think of the holiday and what sort of expectations they have surrounding it. Share your feelings as well, you’ll avoid a lot of awkwardness and embarrassment this way.
If you’re single, gather your single friends and go do a fun activity like Ax Throwing or Top Golf. Host a dinner party or game night. Try to avoid places where couples are likely to be engaging in public displays of affection. If you send yourself flowers to work, the last thing your self-esteem needs is to witness a proposal occur at the next table over.
Stay in and spoil yourself with your favorite take out and a nice bottle of wine. Treat yourself to a day at the spa. Self-care is your first line of defense.
Many of our single clients report feeling excessive loneliness when they don’t have someone to share Valentine’s Day with. But, I have an insider tip to bring you a bit of peace and solace.
Often, this happens because one party desperately wants to celebrate it, but the other party perceives it as a frivolous, made-up holiday. This leads to conflict and disappointment. I always coach my clients to shower your partner with love and affection regularly, not just when you feel a sense of obligation.
Whether you’re happily loved-up, completely alone, or exploring a budding relationship, Valentine’s Day can be stressful. No matter how you choose to spend it, afterward, do a little reflection and make a plan for how you hope to spend the next one.
Ten Luxury Valentine Gifts to Knock Their Socks Off
Luxury Valentine's Gifts for 2021
Struggling to think of ideas for luxury Valentine gifts? Need to really impress your significant other? Is your date’s primary Love Language, Gifts? Then you’ve come to the right place!
We scoured Instagram for ten of the best romantic, high-end products we could find.
Get ready to really wow your partner this Valentine’s Day, but be prepared; you’ll have to do even better next year.
Whether you’re looking for flowers, jewelry, beauty products, or something for your man, we found the perfect items to spoil your better half.
We wouldn’t be a team of Matchmakers if it didn’t come with a bit of advice, though. Typically, our rule of thumb is, if you weren’t dating on New Year’s Eve, we would caution you before going all out with any luxury Valentine gifts.
That being said, relationships tend to move quicker during Quarantine, so use your best judgement, and Happy Shopping!
1. The Cartier Love Bracelet
2. The Mirror
3. The Faceware Pro
4. The Million Roses
5. Lunya Sleepwear & Loungewear
6. Jimmy Choo Slippers
7. Randolph USA Sunglasses
8. Shinola Luggage & Briefcases
9. Manscaped Shave Products
Love Languages in the Time of COVID
Are you familiar with the Five Love Languages? Today, we're going to take a look at all Five Love Languages in the time of COVID, and how to express each of them in a safe and healthy way.
Gary Chapman developed the theory over 25 years ago. The Five Love Languages states that everyone has a preference on how they like to give and receive love.
The Five Love Languages are: Words of Affirmation, Gifts, Acts of Service, Quality Time, and Physical Touch.
Throughout 2020, we have had to adapt and learn new ways to exist in a world where our interactions with other people are more limited and restricted than any other period in modern history.
For single people, this has been particularly challenging. Humans are social animals. Isolation is unnatural and uncomfortable. Lucky for us, we have technology which provides safer alternatives to in-person physical contact. It’s not a perfect system, especially if you’re looking for love.
Words of Affirmation
Let’s start with an easy one, shall we?
It only takes a few seconds of your time to make someone else’s entire day. Compliment the people you care about. Send them a quick text that you’re thinking of them. When they say or do something that makes you happy, tell them so.
The good news is that a global pandemic doesn’t hinder our ability to speak this love language. Whether it’s a Zoom call or a carrier pigeon, it’s important that you make an effort to express your feelings, especially if Words of Affirmation is one of your partner’s primary Love Languages.
Gifts
Luckily, we live in an age where you can have pretty much any good or service delivered to your door quickly and safely. We have options, it’s not just orchids or roses anymore, fellas. So, this is another Love Language that hasn’t been hit too terribly hard by COVID-19.
Gifts need not be expensive or extravagant. Of course, they can be, but the point is to fill your partner’s love tank, not shower her with diamonds. In a world where restaurants and bars are closed, use small tokens and gifts to fill the void caused by the Coronavirus.
Acts of Service
This is where things start to get a little more difficult. Social distancing makes doing the small everyday acts of kindness tougher. This is the best Love Language for creativity and thinking outside the box.
Try to anticipate and alleviate your partner’s pain points to the best of your ability. What is causing her stress at this moment in her life? Is there anything you can do to lessen or eliminate that burden?
Quality Time
I’ve seen a trend online where couples are complaining about having too much Quality Time while they’re on lockdown together.
So, what I want to do is look at the opposite. Single adults who live alone are experiencing the worst of this, in my very humble opinion.
If you don’t have children who live at home, there’s a good chance you’ve spent a significant portion of the last 9 months in complete isolation. I know I have.
How can you spend Quality Time with someone when you’re not allowed to be around them?
Find new ways to do and experience things together. Even if you can’t be in one another’s space, there are safe, socially distant, outdoor activities you can do together.
A lot of places like museums and zoos have added features to their websites where you can do virtual tours and watch live feeds. It’s not the same as being there in-person holding hands, but it’s the next best thing.
Keep in mind, the objective is Quality Time, not necessarily quantity. Your goal is to show her spending time with her and learning more about her is important to you even though it’s not easy to do right now. Women want to see you put in an effort especially when there are barriers to overcome.
FaceTime is your friend. I know the last thing you want to do between back-to-back Zoom meetings is more video calls, but being able to see one another right now is so important. Calls and texts only go so far.
Physical Touch
To all of my Physical Touch people, I know your pain and I wish I could give you all a hug!
My poor dog practically runs and hides when he hears me say the word cuddle these days. We are struggling, but we are surviving!
“Make sure you are taking time to connect physically with your loved ones. Give a shoulder rub. Cozy up as you read a book. Just be mindful to break from the digital routine for some good, old fashioned connection via Physical Touch.”
- Gary Chapman, on Love Languages in the time of COVID
The nation’s top epidemiologists recommend wearing a mask when interacting with anyone outside of your household, this includes during intercourse. So kissing is on hold.
Get creative. One woman built a Hug Glove out of clear plastic with sleeves.
We need to touch and we need to be touched. Depriving oneself of human contact can lead to a decline in both physical and mental health.
I encourage you to lean on Words of Affirmation, Gifts, and Acts of Service during this time. If you’re unable to see one another in person safely, make sure you’re filling each other’s love tanks in other ways, lest the spark die out.
What are your Love Languages in the time of COVID? You can take the quiz here to find out.