These 11 First-Date Questions Can Lead To More Interesting Conversations

Avoid that dreaded lull in conversation.

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Questions to ask on a first date.
Leah Flores, Stocksy

It doesn’t matter how many you go on: First dates are always nerve-wracking. Not only are you hanging out with a brand new person, but it’s also scary to think that you might run out of things to talk about, even if you already know a little bit about each from your dating profiles.

That’s why it’s helpful to go in with a few good questions to ask on a first date, especially the kind that can help you figure out whether you’re truly compatible — while still keeping things fun, of course. After you talk about the weather, the music at the restaurant, and other basics like what you do for work, that’s when you can dive into the deep stuff to see if you’re meant to be.

The kinds of conversations you end up having are determined by the types of questions you ask each other, says Olivia Pelts, MA, LMHC, a relationship therapist and owner of Sunshine City Counseling. If you ask surface-level or yes/no questions, things will fizzle out fast, and it’ll make for a very boring date.

Even if you don’t end up running away into the sunset together, it’s worth it to aim for a lively chat when you meet up with a potential S.O. Below, experts shed light on what to ask your date the first time you hang out.


“What do you do to relax and unwind?”

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To get an idea about how your date spends their time off, ask how they like to relax and unwind after a tough day. “This question offers a glimpse into your date's self-care habits and allows them to share activities they enjoy, potentially leading to conversations about shared interests and opportunities for future dates,” says Pelt. “It also says a lot about their mindset of what it means to need to unwind and what a ‘long day’ is for them.” Who knows — you might realize your energy levels are perfectly matched.


“Are you close with your family?”

Another way to get the scoop is to ask about their family life, says Michael Kaye, the global communications manager at OkCupid. If they’re comfortable talking about it, you’ll get to hear about how they grew up, family traditions, how often they see their parents, etc.

For a lot of people, this is super important. "On OkCupid, 84% of women and 79% of men say they're close to their family, and a majority of people say it's important their families get along with each other,” Kaye tells Bustle.

It’s important not to make snap judgments, since people come from all walks of life — but a first date is the perfect time to ask questions that’ll help you realize the potential a relationship has, and the way your date relates to the people closest to them.


“What’s your best friend like?”


There’s a saying that you are the culmination of the five people you spend the most time with, and that’s why “getting to know your date's closest friendships will give you a decent idea as to what type of person they are," says Shank.

If your date surrounds themselves with partiers, sports fans, or artists, it’s possible they share a lot of the same interests and energy levels. It can be an eye-opening question, as well as one that gets a conversation going about the importance of friendship in your lives.


“What’s your biggest achievement or one you’re most proud of?”

This question might make your date a little sheepish — or it might set them off on a monologue about their achievements. Either way, it'll be a cool intro to the kinds of things they focus on and what’s important to them.

"This is one of my favorite questions to ask friends, family, and dates," Shank tells Bustle. It tells a lot about a person and helps you get to know them on a deeper level — two things that are pure gold on a first date.


“What kind of relationship are you looking for?


Trust: This doesn't have to be an interrogation. You can even casually ask what brought them to the dating site you might have met on, or if they go on dates often — or simply what type of relationship they’re looking for, says Dr. Fran Walfish, a psychotherapist in private practice in Beverly Hills, California. It should be fairly easy for them to answer. "If they are unwilling to open up about this, it is a definite red flag," she tells Bustle.


“What are your thoughts on the upcoming election?”

"Among OkCupid users, 84% of people want to discuss politics with their partner and 58% of people prefer their date share the same political beliefs as them," says Kaye. So if you can find a way to sneak it in, perhaps by chatting about an upcoming election, go ahead and do it.


“What was your top song on your Spotify Wrapped last year?”

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Don't forget to keep things light and fun by asking each other silly stuff, too. Their Spotify Wrapped can be particularly interesting, since lots of people’s music taste matches their personality. And if it doesn’t, even better. You’ll end up talking for hours about why they had a TikTok sound as their number one.


“What do you think about this paint color?”

Sameera Sullivan, a matchmaker and a relationship expert, suggests asking for advice. Whether you ask what paint color they’d choose for your remodel, how they’d handle a certain issue, or where’s the best pizza place in town, it’ll be a cute moment to test how you might operate as a couple. “Asking them for advice is a fantastic way to gain their trust and get them to open up to you,” Sullivan tells Bustle.


“If you had an entire day to yourself, what would you do?”

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“This question prompts your date to reveal their passions and interests, providing you with an opportunity to discuss hobbies and personal goals,” Pelts says. If they bring up something fun, like how they enjoy going to concerts, it also makes it easy to suggest future plans to meet up.


“What’s your favorite vacation spot?”

Susan Trombetti, a matchmaker and CEO of Exclusive Matchmaking, recommends following up tough questions with something light, especially since you don’t want a date to feel like an interrogation. “Asking about their favorite vacation or hot travel spots are fun things to talk about,” she tells Bustle. “You want to keep the conversation light and fun while also getting to know the person — so see if you really connect when you speak about positive topics.”


“What were some of the toughest parts of your last relationship?

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If the date is going well and you can kind of see a future — and you’re feeling really bold — that’s when you might want to bring up the past. According to Pelts, this question will help you understand how they dealt with difficulties in their last relationship, and it’ll provide clues about their problem-solving skills and relational patterns.

“It offers an opportunity for them to share their experiences and reflect on their own role in the dynamics of previous relationships, too,” she says. Are they owning what went wrong? Or completely blaming their ex? These are the things you need to know — and it’ll definitely make for an interesting chat.


Olivia Pelts, MA, LMHC, relationship therapist, owner of Sunshine City Counseling

Michael Kaye, global communications manager at OkCupid

Dr. Fran Walfish, psychotherapist in private practice

Sameera Sullivan, matchmaker, relationship expert

Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking

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