Illustrated by: Abbie Winters
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.
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.
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.”
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.”
What’s the most rebellious thing you’ve ever done?
“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!”
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.”
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.”
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?”
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!”
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!”
What was your quirkiest habit as a kid?
“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.”
“Humility is important to me, and it’s interesting to hear how people got to the place they are today.”
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!”
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.”
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!”
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.”
How are you getting home?
“What better way to seal the deal, if you know what I mean?”
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.)”
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!”
Do you like coffee or tea?
“How else will I know what to make for you in the morning?”
“It’s fairly important to me that someone I date has ambitions and has ‘a zest for life,’ if you will.”
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!”
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.”
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.”
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.”
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!”
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.'”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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?!”
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.'”
What’s your favorite TV show?
“First things first: Find out if you’re binge-compatible.”
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.”
Who would play you in the movie of your life?
“You can tell a lot about someone by how they answer this question.”
Do you like reality TV?
“I ask because I love it, and anyone who knows about the Kardashians or Real Housewives gets brownie points.”
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