Matchmaker Says: Let’s Give Em’ Something to Talk About

It's been two whopping years since What To Tawk About was published, and in light of recent reader inquiry, we've decided to dust off our talking-point boots to help busy singles everywhere achieve convivial conversations...

It’s been two whopping years since What To Tawk About was published, and in light of recent reader inquiry, we’ve decided to dust off our talking-point boots to help busy singles everywhere achieve convivial conversations. 

In short, good date conversation starters can’t be answered with a simple “yes” or “no,” but are open-ended, with the power to spark a conversation that might last for hours. 

To kick us off, here’s the short list:

  1. What was the last really great book you read?

  2. What do you enjoy doing in your free time?

  3. What is your favorite movie, or the best one you saw lately?

  4. Tell me about your best friend(s), why are you two such good buddies?

  5. Do you have pets? Tell me about them.

  6. What’s the last thing you did that surprised you?

Interesting side-note — an OKCupid analysis from 2011 reports the three most common questions long-term couples ask (and agree on), during first dates are:

  1. Wouldn’t it be fun to chuck it all and go live on a sailboat?

  2. Do you like horror movies?

  3. Have you traveled around a foreign country alone?

Hmm… interesting. And if you need a refresher on what not to talk about, check out, Matchmaker Says: Just Don’t Ask

Now to the good stuff. 

Matchmaker Dorothy Stover digs in:

How do you converse with your date without it feeling like an interview? This is a very common question I hear from clients and friends. My answer is always the same:

Be a present, active listener and the conversation will flow.
Answer questions by telling stories.

What does it mean to be present? Listen. Focus on your date — not on the food, or your server, or your phone. What is the person across from you actually saying? If you ask your date how their day has been and they respond with, a little rough because of public transportation delays — notice that. Most of us have been there. Agree and be interested.

Taking Interest in someone leads to interesting conversation, and ultimately greater connection.

Share a story of yours about public transit. Storytelling opens the doorway to finding common ground. Moreover, when you share a personal story it makes your date feel comfortable to share as well.

Also important, try to avoid replying to questions with one-two word answers. Elaborate! I’m not suggesting you ramble on unnecessarily in response to every prompt, but give a bit more than a solid yes or a no so you achieve reciprocal dialogue. 

So, what do you talk about?

I have found the topic of travel to be a universal connector. Even if your date has not traveled a great deal, they have likely dreamed about where they would go. Ask them where they have been, where they are going or where they’ve always dreamed of going. If you find you share the same dreams, let them know. 

The more you reveal to each other, the better. 

I like to ask: What is something no one really knows about you? 

This question is best asked when you’re starting to feel that intangible (and magical) chemistry building.

If they seem nervous, offer to go first. Then share something not many people (if anyone) knows about you. Perhaps a fear, a habit, something you long for, a dream or a regret. Be vulnerable and honest.

As an example, I’ll share something about myself that not many people know (but, will now!): 
I have a fear of the water, but love to swim! As a young child, I exclusively clung to a friend or family member’s back when in the water. As an adult, I don’t go in the water without company. This almost certainly has something to do with the movie Jaws! 

Matchmaker Remy Boyd continues:

First dates are awkward, whether you know the person or not. Finding the ideal ice breaker can be a challenge, but the goal remains — to get to know your date. For brave souls who want to delve deeper, here are my favorite questions to reveal your date’s mindset (and maybe also long-term goals).

“Do you like to date?” 
I know, you’ve likely been advised not to talk about dating while on a date! And I agree with that, but this specific question when asked in a curious way can open a pandora’s box of dialogue between you and your date. With this question you have the opportunity to learn about his or her dating history, preferences and relationships (generally speaking), without the unpleasantness that direct probing into these topics may yield. It is a brave question, but the reward can be great! 

“What couple do you admire and why?” 

The couples we admire say a lot about our own relationship goals.

If your date identifies his or her parents and/or grandparents as a source of admiration, that says a lot (i.e. they have real-world relationship applications to admire, boding well for their partnership sensibilities as well). If a celebrity couple is mentioned, this may indicate a level of fantasy around relationships that is unrealistic.

“What do you think is the best way to get to know someone?” 
This is a great question to see how adventurous, spontaneous or stuck in the mud your date is. The answers provided may turn you off, but that’s OK. Wouldn’t you rather know that your date’s relationship-building leanings aren’t for you before investing more time? 

Matchmaker Melissa Rogers weighs in:

I like to ask questions that allow my date to authentically share who they are. Asking about an occupation can only get you so far, right? 

There are two questions I ask clients upon our first meeting that always result in the most honest and interesting responses! In fact, when I ask these questions I typically “hear” a smile from on the other end of the phone.

First, I ask what type of genre they enjoy binge watching as a guilty pleasure. Sounds a little silly, but it gives me a peek into the mind of my client. Some love true crime documentaries, some could watch every episode of The Office 5 times over and never get sick of it. What I find is that you can get a sense of a person’s style of humor, their intellect, or even their overall attitude.

Someone who is drawn to murder mystery thrillers is very different from someone who wants to casually unwind with The Bachelor on in the background.

Of course, this question also lends a hand in discovering how people spend their free time. Perhaps you’ll hear, “I don’t own a TV” or “I’d rather read a book.” It’s an open-ended question that may allow you to bond over shared interests, or provide a path to dig deeper.

I also ask: “If you were to die tomorrow, what would your final meal be?” It’s silly, it’s light-hearted, it makes people laugh. So what if it doesn’t reveal how many kids they want to have or if they invest in a Roth IRA? It allows you to stay in the moment, gives a hint at their favorite cuisines (for the second date, of course!), and disarms them in general. Plus, the answers are always fun!

Matchmaker Coree Schmitz concludes with a simple question to leave you thinking

Date conversation often centers around our careers. I am happy for those that love what they do, but many are not defined by what they do during the work day. So, I like to ask:

“What do you love?”

The choice of words alone catches people off-guard, which I believe helps elicit a more honest response.

Sharing what you love opens the door for commonalities, conversation, and compassion. I think it makes people feel more real and reminds all of us that we are more than a professional title.

Things that I personally love include époisses cheese, the rush I get when I buy a plane ticket, learning a new word in Spanish, and going to see anything live (music or theater). What do you love? 

Subscribe to
our newsletter

    Popular Posts