7 relationship experts reveal their favourite questions to avoid awkward small talk on a first date

NetflixHere’s how to get through awkward ‘small talk’ on a first date.
  • Making meaningful small talk on a first date can get tricky and awkward.
  • Relationship experts told Business Insider their favourite questions to ask on a first date.
  • Many of them stressed that to have the conversation flow organically, you should be present in the moment by asking good follow-up questions.
  • Visit Business Insider’s homepage for more stories.

Making small talk can be awkward – especially on a first date.

Simply asking “So, what do you do?” isn’t going to lead to the meaningful conversations you want to have on a first date to ensure there’ll be another one.


Read more:


13 simple ways to get better at small talk

To help break the ice with a stranger on a first date, Business Insider asked seven relationship experts from across the country to reveal their favourite questions to ask on a first date.

While many of them had a few pre-determined questions at hand, they said the most important thing to keep in mind is just to be a good listener, and to be yourself.

“Meaningful small talk is virtually anything that helps you connect with the other person in a genuine way,” Shira Teichman, a dating coach and cofounder of the dating app Forj, told Business Insider. “Ask what feels natural in the moment, without calculating what you think you’re supposed to say.”

For those who need a little extra guidance, here are the best questions to ask on a first date, according to relationship experts:


What do you think of the restaurant/bar/etc. we’re at?

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“Be present in the moment,” says Claudia Duran, a relationship expert based in Miami, Florida. To get the conversation rolling, she recommends sharing your experience of the date as soon as it starts by asking about the vibe of the restaurant or bar. If you both notice something odd – like another couple on a date that doesn’t seem to be going well – go ahead and bring that up to establish a shared experience.

“[Being] present for the moment and present to sharing them together opens up the dialogue organically,” Duran adds.


If you met on a dating app, ask about what led you to accept their profile.

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Right off the bat, you want to establish a common connection with your date, says Andrea Syrtash, dating expert and co-author of “It’s OK to Sleep With Him on the First Date: And Every Rule of Dating Debunked.” Finding something you can both relate to will naturally lead itself into a good conversation.

While making plans with someone you met online can be awkward right off the gate, bringing up something you saw helps to minimise that discomfort.

“At the end of the day, why are you attracted to someone on an app? Because you’re swiping and you’re like, ‘Hey, I liked the way he looks,'” New York City-based relationship expert Rori Sassoon told Business Insider. “You know nothing about that person.”


What are your hobbies?

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Marla Mattenson, founder and CEO of Mattenson Coaching & Consulting, told Business Insider she always recommends you ask your first date, “What are you kind of obsessed with these days?”

While asking about where someone works might lead to dead-end conversations, inquiring about a person’s hobbies or interests outside of their office gives you a better sense of their values, Sassoon said Business Insider.

“I think that you get to learn a lot about a person when you understand what their passions and their hobbies are,” she added. “It’s a light question, not too heavy.”


Do you drink?

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A first date is also a good time to get to know the other person’s lifestyle choices – especially ones that could cause problems down the road, Duran says.

If one person is vegan, for instance, and the other loves steak, that might be a deal breaker for one party. The same is true for alcohol. If you’re a recovering alcoholic, for instance, you may not want to spend too much time with a big party-goer. “Those kinds of things should be open,” she said. “That’s who we are.”

While Duran stresses you should keep an open mind when getting to know someone, if you know a certain lifestyle would not match yours, go ahead and ask right away.


What would be the one value you would say is really important for you to live by?

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“The best questions to ask on a first date are those that gauge your basic level of compatibility with your date, dig out shared values, help both have clarity on what the other person is looking for, and build a decent level of intimacy,” Sami Wunder, a certified relationship coach, told Business Insider in an email.

While basic questions about someone’s personal life can build intimacy and help figure out whether you two are compatible, understanding shared values might take some direct questioning.


Ask good follow-up questions.

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Teichman recommends you don’t go in with a set of prepared questions, as you don’t want to come across as too calculated. She added that many of her clients complain about wanting to skip the “small talk” and instead have meaningful conversations on first dates. While she understands that first-date conversations can be awkward, she said asking good follow-up questions forces you to be attentive to what the other person is saying.

“It’s not really about choosing the right subject matter,” Teichman told Business Insider. “It’s about the effort you make to bring your whole self on the date.”


Where did you grow up?

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While intimate questions about family and past relationships can be too invasive for a first date, asking light questions about where they grew up can lead to more meaningful conversations. “It sounds a little boring, but all these leading questions are simply for a response that you can then build from,” said New York City-based relationship expert and love coach Susan Winter.

Plus, getting a better sense of their relationship with their friends and family can clue you into how this person would be in a relationship, Sassoon said.

“When you know that a person has friendships that lasted many years, they are in a healthy state to have sustainable relationships,” she added.

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