In the best-case scenario, you go on a first date with someone, and you hit it off. The chemistry is off the charts, and you're never at a loss for what to talk about.
Sometimes (okay, most of the time), though, first dates aren't smooth sailing. That doesn't always mean you're incompatible — just that we are humans, and dating can be awkward. It can be hard to figure out what to ask without making it seem like you're interrogating your date. After all, the key to a good date is relaxed conversation, and the last thing you want is to recreate the beginning of this scene from The Holiday, in which Cameron Diaz essentially makes Jude Law's palms sweat from her interview-like first-date demeanor.
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But whether you're trying to fill an awkward silence or just trying to get to know your date better, we have you covered. We sent out an anonymous survey to get people's best, most creative first-date questions. Ahead are the ones that stood out to us most. Check them out, and if you want, leave a comment with some of your own go-to conversation-starters.
Do you consider yourself an introvert?
"I am definitely an introvert, and tend to feel a little uncomfortable on a first date with a complete stranger. Understanding how the other person operates in their world — do they command a room or are they a wallflower? — can help me connect with them a little deeper."
"I am definitely an introvert, and tend to feel a little uncomfortable on a first date with a complete stranger. Understanding how the other person operates in their world — do they command a room or are they a wallflower? — can help me connect with them a little deeper."
Do you like working out?
"Fitness is important to me and a big part of my lifestyle. They don't have to be a meathead or into CrossFit, but I would like to go on a run or take a yoga class instead of dinner dates sometimes."
"Fitness is important to me and a big part of my lifestyle. They don't have to be a meathead or into CrossFit, but I would like to go on a run or take a yoga class instead of dinner dates sometimes."
What's your guilty pleasure TV show?
"It gives me a glimpse of their real personality. Personally, I love watching hours of Fixer Upper."
"It gives me a glimpse of their real personality. Personally, I love watching hours of Fixer Upper."
Who did you vote for?
"Yes, really. It's best to get this question over with right away. And if they don't have an answer that I agree with, that's okay, because it means we can have a riveting conversation on an otherwise boring first date."
"Yes, really. It's best to get this question over with right away. And if they don't have an answer that I agree with, that's okay, because it means we can have a riveting conversation on an otherwise boring first date."
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What was the first concert you ever attended?
"It's a subtle way to get an idea of their tastes. Were they an N'Sync fan or Backstreet Boys stan? And can I make fun of them for that?"
"It's a subtle way to get an idea of their tastes. Were they an N'Sync fan or Backstreet Boys stan? And can I make fun of them for that?"
Were you involved in Greek life?
"Frats and sororities were a Big Deal at my college, and loyalties can run deep."
"Frats and sororities were a Big Deal at my college, and loyalties can run deep."
What's your favorite dating app?
"We don't have to pretend we don't use dating apps, and everyone has an opinion about what the different apps have to offer."
"We don't have to pretend we don't use dating apps, and everyone has an opinion about what the different apps have to offer."
Can you cook?
"I think it's attractive when someone feels confident around the kitchen, and cooking together is usually a good and inexpensive second date."
"I think it's attractive when someone feels confident around the kitchen, and cooking together is usually a good and inexpensive second date."
Are you close with your roommates?
"I still live with my friends from college, so I like to hear about other people's living situations. Plus, if I'm going to be walking into a frat house, I need a fair warning."
"I still live with my friends from college, so I like to hear about other people's living situations. Plus, if I'm going to be walking into a frat house, I need a fair warning."
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Do you have a go-to drink?
"This is the most basic icebreaker in the game, but it works. Some people really think they identify with an Old Fashioned like they're Don Draper or something."
"This is the most basic icebreaker in the game, but it works. Some people really think they identify with an Old Fashioned like they're Don Draper or something."
What's the most rebellious thing you've ever done?
"I am not that daring, but I do like rebels."
"I am not that daring, but I do like rebels."
What was your favorite TV show growing up?
"I'm a sucker for nostalgia and this is a light topic that usually makes people chatty. And who knows? Maybe they'll understand my obscure Sailor Moon references!"
"I'm a sucker for nostalgia and this is a light topic that usually makes people chatty. And who knows? Maybe they'll understand my obscure Sailor Moon references!"
Are you into astrology?
"The followup question is then always, 'What's your sign, what time were you born, and can I read your birth chart?' But those I save for the second date."
"The followup question is then always, 'What's your sign, what time were you born, and can I read your birth chart?' But those I save for the second date."
What's one thing that you're looking forward to next week?
"I like to know what people like to do for fun, but asking 'what are your hobbies' is sort of weird. Then if there's something cool that they are doing in the future, I have an excuse to message them again."
"I like to know what people like to do for fun, but asking 'what are your hobbies' is sort of weird. Then if there's something cool that they are doing in the future, I have an excuse to message them again."
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Did any of your former classmates end up becoming famous?
"This is a good icebreaker question, because people usually have at least one person from their town who made it big, and they almost always have a funny story about it. Or they grew up with all famous people, which would also be very interesting?"
"This is a good icebreaker question, because people usually have at least one person from their town who made it big, and they almost always have a funny story about it. Or they grew up with all famous people, which would also be very interesting?"
Are you pro-social media or against it?
"Not going to lie, I usually look up my matches on social media before we go on a date, but I like to know what they think of social media in general. Are they the type to want to Snapchat everything we do? Can I find anything about their exes on their Insta? This is the important stuff!"
"Not going to lie, I usually look up my matches on social media before we go on a date, but I like to know what they think of social media in general. Are they the type to want to Snapchat everything we do? Can I find anything about their exes on their Insta? This is the important stuff!"
Where do you want to travel solo?
"If money and vacation time off from work weren't any issue, I like to ask where you would travel with: your best friend, your love, and by yourself. I like to do things alone — it's not weird!"
"If money and vacation time off from work weren't any issue, I like to ask where you would travel with: your best friend, your love, and by yourself. I like to do things alone — it's not weird!"
What was your quirkiest habit as a kid?
"I feel like it always loosens people up — childhood is fun!"
"I feel like it always loosens people up — childhood is fun!"
How did you come out?
"It gives me a sense of how they grew up and also how they handle a big, stressful, life-changing situation. It usually ends up coming up in conversation, but I find myself steering it that way, and then asking when it seems right or normal to."
"It gives me a sense of how they grew up and also how they handle a big, stressful, life-changing situation. It usually ends up coming up in conversation, but I find myself steering it that way, and then asking when it seems right or normal to."
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What's the weirdest job you've ever had?
"Humility is important to me, and it's interesting to hear how people got to the place they are today."
"Humility is important to me, and it's interesting to hear how people got to the place they are today."
Illustrated by: Abbie Winters
What's your favorite food?
"I spend a good chunk of my waking hours either eating or thinking about food, so I like knowing what other people are eating!"
"I spend a good chunk of my waking hours either eating or thinking about food, so I like knowing what other people are eating!"
What's your most embarrassing New York City story?
"The Big City can be a very weird place whether you live here or have only visited. This lets me see if the guy takes himself too seriously and is able to laugh at himself. It's also an easy way to tell if he's a good storyteller (which is important to me!). I like when people ask about memories or stories, because it's a very concrete way to relate to someone, and it gives people insight about your personality by the details you includes and the mannerisms you use to tell the story."
"The Big City can be a very weird place whether you live here or have only visited. This lets me see if the guy takes himself too seriously and is able to laugh at himself. It's also an easy way to tell if he's a good storyteller (which is important to me!). I like when people ask about memories or stories, because it's a very concrete way to relate to someone, and it gives people insight about your personality by the details you includes and the mannerisms you use to tell the story."
Illustrated by: Abbie Winters
Where have you traveled?
"I love to travel myself, so I want to know if the person I'm dating has been to interesting places, or is open to jet-setting with me!"
"I love to travel myself, so I want to know if the person I'm dating has been to interesting places, or is open to jet-setting with me!"
Are you into sports?
"You can hit them up when a game is on, and if they don't like the same teams as you, a little friendly competition can turn into fun banter."
"You can hit them up when a game is on, and if they don't like the same teams as you, a little friendly competition can turn into fun banter."
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Illustrated by: Abbie Winters
How are you getting home?
"What better way to seal the deal, if you know what I mean?"
"What better way to seal the deal, if you know what I mean?"
Illustrated by: Abbie Winters
Who is your favorite Kardashian?
"The answer to this question will tell you everything you need to know about a person. (Hint: The correct answer is always Kim.)"
"The answer to this question will tell you everything you need to know about a person. (Hint: The correct answer is always Kim.)"
Illustrated by: Abbie Winters
Do you like reality TV?
"It's totally cool if the person I'm dating isn't into The Bachelor or anything, but they have to respect that I am!"
"It's totally cool if the person I'm dating isn't into The Bachelor or anything, but they have to respect that I am!"
Illustrated by: Abbie Winters
Do you like coffee or tea?
"How else will I know what to make for you in the morning?"
"How else will I know what to make for you in the morning?"
Illustrated by: Abbie Winters
What's on your bucket list?
"It's fairly important to me that someone I date has ambitions and has 'a zest for life,' if you will."
"It's fairly important to me that someone I date has ambitions and has 'a zest for life,' if you will."
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Illustrated by: Abbie Winters
What's your favorite song to dance to?
"I've been known to tear it up on the dance floor, and I need someone who can keep up!"
"I've been known to tear it up on the dance floor, and I need someone who can keep up!"
Illustrated by: Abbie Winters
Who in your family are you closest to?
"I have a soft spot for mama's boys. More often than not, it shows that they can respect women — uh, just as long as he's not too close to his mom."
"I have a soft spot for mama's boys. More often than not, it shows that they can respect women — uh, just as long as he's not too close to his mom."
Illustrated by: Abbie Winters
Are you a morning person or a night person?
"This works because it helps to see if your schedules align, or if you're destined to be up cooking breakfast alone while your potential S.O. sleeps in."
"This works because it helps to see if your schedules align, or if you're destined to be up cooking breakfast alone while your potential S.O. sleeps in."
Illustrated by: Abbie Winters
Who do you live with?
"This might be more of an NYC/big city question but since most people these days can't afford to live alone, it's always good to suss out your date's living situation — in case you'll one day be meeting these roommates."
"This might be more of an NYC/big city question but since most people these days can't afford to live alone, it's always good to suss out your date's living situation — in case you'll one day be meeting these roommates."
Illustrated by: Abbie Winters
Tell me about your friends.
"Friends of friends are often hit-or-miss, and unfortunately, friends-of-significant-others can be even more hit-or-miss. That being said, it's good to try to feel out a potential S.O's friends early on!"
"Friends of friends are often hit-or-miss, and unfortunately, friends-of-significant-others can be even more hit-or-miss. That being said, it's good to try to feel out a potential S.O's friends early on!"
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Illustrated by: Abbie Winters
What books have you been into lately?
"It's like John Waters said: 'If you go home with somebody and they don't have books, don't fuck them.'"
"It's like John Waters said: 'If you go home with somebody and they don't have books, don't fuck them.'"
Illustrated by: Abbie Winters
Are you more of a cat or dog person?
"I am vehemently a cat person and I need a potential S.O. to be cool with that."
"I am vehemently a cat person and I need a potential S.O. to be cool with that."
Illustrated by: Abbie Winters
What do you like to do when you're not working?
"I feel like living in NYC, everyone is pretty much married to their jobs, but even if you really love what you do, you've gotta have a life outside of that."
"I feel like living in NYC, everyone is pretty much married to their jobs, but even if you really love what you do, you've gotta have a life outside of that."
Illustrated by: Abbie Winters
What kind of music do you listen to?
"Ask anyone who knows me: Music is the biggest part of my life. I love being able to share that with someone. If we don't [already] have any favorite artists in common, [introducing them to new stuff] can be a really great way to get to know each other."
"Ask anyone who knows me: Music is the biggest part of my life. I love being able to share that with someone. If we don't [already] have any favorite artists in common, [introducing them to new stuff] can be a really great way to get to know each other."
Illustrated by: Abbie Winters
Describe yourself in one word.
"It sounds really interview-y, so I only pull this one out when the conversation is dying and I'm trying to revive it."
"It sounds really interview-y, so I only pull this one out when the conversation is dying and I'm trying to revive it."
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Illustrated by: Abbie Winters
How did your parents meet?
"Everyone loves a great story! Asking how someone's parents met opens the conversation to their relationship with their parents."
"Everyone loves a great story! Asking how someone's parents met opens the conversation to their relationship with their parents."
Illustrated by: Abbie Winters
Where do you work?
"Maybe it's a little boring, but I always like to ask where someone works, or what they do for a living. I feel like it opens the conversation and then you can find out if they're passionate about what they do, and if not, what they would rather be doing instead."
"Maybe it's a little boring, but I always like to ask where someone works, or what they do for a living. I feel like it opens the conversation and then you can find out if they're passionate about what they do, and if not, what they would rather be doing instead."
Illustrated by: Abbie Winters
If you could visit any time period in all of history, what would it be?
"I'm a huge history buff, so I like knowing what everyone else's favorite historical period is! Plus, I like to think it's a thought-provoking question that'll spark some good conversation."
"I'm a huge history buff, so I like knowing what everyone else's favorite historical period is! Plus, I like to think it's a thought-provoking question that'll spark some good conversation."
Illustrated by: Abbie Winters
What movies have you been interested in recently?
"Okay, someone's taste in movies isn't the be-all, end-all, but it does tell you a little more about them. Are they a Pulp Fiction fan, or are they more Animal House? Or both?!"
"Okay, someone's taste in movies isn't the be-all, end-all, but it does tell you a little more about them. Are they a Pulp Fiction fan, or are they more Animal House? Or both?!"
Illustrated by: Abbie Winters
What's your relationship with your family like?
"This isn't so much a question as a socialization philosophy. I like to be as real as possible with people on a first date. Recently, it was 'What's your relationship with your family like? Oh, it's bad? Mine too. Tell me more.'"
"This isn't so much a question as a socialization philosophy. I like to be as real as possible with people on a first date. Recently, it was 'What's your relationship with your family like? Oh, it's bad? Mine too. Tell me more.'"
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Illustrated by: Abbie Winters
What's your favorite TV show?
"First things first: Find out if you're binge-compatible."
"First things first: Find out if you're binge-compatible."
Illustrated by: Abbie Winters
Where did you grow up?
"If you're on a first date and you want to get to know the person, start by asking about who they are and where they grew up."
"If you're on a first date and you want to get to know the person, start by asking about who they are and where they grew up."
Illustrated by: Abbie Winters
Who would play you in the movie of your life?
"You can tell a lot about someone by how they answer this question."
"You can tell a lot about someone by how they answer this question."
Illustrated by: Abbie Winters
Do you like reality TV?
"I ask because I love it, and anyone who knows about the Kardashians or Real Housewives gets brownie points."
"I ask because I love it, and anyone who knows about the Kardashians or Real Housewives gets brownie points."
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