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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.
How are you getting home?
“What better way to seal the deal, if you know what I mean?”
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!”
Illustrated by: Abbie Winters
Do you like coffee or tea?
“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.”
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.)”
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!”
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.”
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.”
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.”
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!”
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!”
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.’”
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.”
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.”
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.”
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.”
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.”
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.”
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.”
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?!”
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.’”
Illustrated by: Abbie Winters
What’s your favorite TV show?
“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.”
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.”
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.”
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!”
Illustrated by: Abbie Winters
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