9 Questions To Ask Someone On A First Date If You've Never Met Them Before

by Laken Howard

If you're someone who tends to get nervous on first dates, imagining how well — or not well — the conversation with your date might go can be a major source of pre-date stress. The good news? As long as you have an idea of some questions to ask on a first date, you can turn any lull into lively conversation. Particularly if you're meeting a blind date (do people still do that?) or someone you matched with on a dating app, it's nice to have a backup plan when it comes to what to talk about on a first date — because no one wants to endure an awkward silence with a total stranger.

"When you’re meeting a friend of a friend, chances are you’ve gotten at least a little intel about what to expect, or you’ve met them in passing before," Scott Valdez, founder and president of ViDA, a service that helps clients meet their ideal match online, tells Bustle. "But when you’re meeting a total stranger, your date is forming a first impression... Asking open-ended questions is essential to keeping a conversation out of 'awkward pause' territory."

Making a point to ask more thoughtful, open-ended questions — instead of simply sticking to the basics like 'where do you work?' or anything with a yes/no answer — is a great way to get to know your date and form a connection. That being said, you shouldn't treat your convo like an interrogation: don't dole out ~deep~ questions for your date to answer if it doesn't feel natural. If you're having trouble getting the conversation started with a stranger, here are nine questions to ask on a first date with someone you've never met.


"What Are You Most Proud Of?"

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Assuming your date hasn't already been humble-bragging all through the appetizer course, asking them to share something they're proud of can be a great way to find out what they value: will they talk about a professional achievement or something more personal?

"This icebreaker serves as a chance for your date to show off [their] accomplishments and as a means for learning more about [their] background," Justin Lavelle, Relationship expert and chief communications officer for BeenVerified, tells Bustle. "Your date may mention graduating from school, finding the perfect career, volunteer work, buying [their] dream car, etc. However big or small, whatever your date is most proud of alludes to [their] values."


"Is There Anything You're *Not* Proud Of?"

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On the flip side, asking your date to share a moment they're not so proud of can be really revealing as well. Just be sure not to ask it in a prying way, and clarify that they can answer as seriously (or not) as they want — you can even go first and set the tone by sharing something hilarious and innocent like, 'I once stole a candy bar as a kid.'

"Most people are not keen on sharing personal information that may offset another person’s positive image of them," Lavelle says. "[However], this question opens the door to learning a little about some experiences/behavior in your date’s past that might be less than desirable so you have a better picture of the total person."


"What Hobbies Keep You Busy?"

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Asking someone about their hobbies and passions is a sure-fire way to get them talking, and this question also has the added bonus of giving you some insight into how your date spends their free time — and how you might fit into that schedule someday.

"What makes your date tick?" Lavelle asks. "Snowboarding? Fishing? Painting? Collecting coins from other countries? Before the end of your first date, you want to find out your date’s passions. Hobbies define self-identity, build confidence, and relieve stress. You do not need similar hobbies for compatibility, but you both should have at least one for a healthy relationship."


"What Does Your Ideal Relationship Look Like?"

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This question should be treated with caution — don't ask it if it feels 'too soon' or like the date isn't going well, Lavelle says — but asking someone to share what they're looking for in a partner or what their ideal relationship looks like is a good way to see if you'd be romantically compatible.

"Discussing relationship goals and aspirations is crucial for deciding if couples should continue pursuing each other," Lavelle says. "One person may want something light, fun, and exciting; whereas the other is looking for something serious and worth investing in. While the first date is too early to talk compromises, figuring out what your date sees as important in a relationship may answer the question, 'Should I ask [them] out on a second date?'"


"What Made You Want To Meet Up?"

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While it's not really a good look to fish for compliments from your date, if you're tactful in how you ask, getting your date to open up about what drew them to you and made them want to meet up with you IRL can give you a lot of insight into their personality and motivations.

"This question gets to someone’s core motivations and also gives them an opportunity to let you know their impression of your online profile or text messages (anything pre-meetup)," Rachel Wright, psychotherapist and therapeutic relationship coach, tells Bustle. "Someone could answer this with 'your looks,' or 'the way you explained your favorite book intrigued me.' This feedback gives you a glimpse into their priorities as well as how you are being perceived through your online profile (which is super helpful information!)."


"Tell Me About Your Best Friend."

Hannah Burton/Bustle

The company someone keeps says a lot about them, as does the way they talk about the special people in their lives. Asking a date to describe their relationship with their BFF is a great way to get them talking while also getting a glimpse into who they are and what they value in a friendship.

"You can tell a lot about somebody by their friends and how long they’ve been friends with their close friends," Wright says. "So, saying something like 'tell me about your closest friends,' will help you get a deeper and wider look at your date’s life and what it may look like to date them. Plus, how they speak about their friends or family is how they would most likely speak about you if you were in this person’s life!"


"Why Do You Think You're Single?"

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Tread carefully, because this question can come off as a little insensitive, but as long as you clarify that you just want to hear a bit about where your date is in their romantic journey — instead of expecting them to list off their negative qualities — this question can be super insightful.

"OK, so this question does sound a little weird or judgy, [but] it’s not meant to be that way at all," Wright says. "This question allows you to see the world through your date’s eyes for a moment. There are many different answers to this question, and they all have pretty different meanings. 'I haven’t found the person for me,' versus 'I’m super picky,' versus 'No one is good enough for me' — you get [the idea]."


"What Was It Like Growing Up In Your Family?"

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Everyone is influenced in some way by their upbringing — how you were raised, your family dynamic, etc. — and asking your date to talk about what their life was like growing up can give you an important look into who they are at their core.

"This question touches on a personal topic but is framed pretty broadly," Christine Carpenter, PsyD, dating and relationship consultant at Evolve Dating, tells Bustle. "It is easy for the recipient [to] share as much or as little as they wish on the topic. The level of what is revealed is as good to know as the content of the response."


"What Drew You To The Profession You're In?"

Andrew Zaeh for Bustle

Asking someone to talk about work on a date might sound like a fast-track to boredom, but someone's career is a huge part of who they are, so it can be illuminating to figure out why they chose the path they did — or what they might want to do differently in their professional future.

"Again, there is potential to learn something a little deeper about your date depending on what they are comfortable sharing but it isn’t so personal that it would be experienced as intrusive," Carpenter says.

Ultimately, the key to getting to know a total stranger on a first date is simple: be inquisitive, but not pushy. The more open-ended questions you ask, the more opportunities you'll have to hear enlightening anecdotes and learn more about your date — that way, you'll be better equipped to make a judgment about whether or not you want to go on a second date.