30 Funny Questions To Ask Your Date

By Griffin Wynne

31 August, 2021

Let's say you're forty minutes into a relatively solid date when the conversation comes to a lull. A drink and a half down, you’ve covered hometowns and siblings, bad bosses and slob-y roommates, and playfully debated how old Lorde is, only to clear it up with Google.

You know you’re funny. Your friends always post your texts in their stories! You send the best GIFs in Slack! But you can’t seem to gauge your date’s humor. Rest assured, you don’t have to put on a standup set or break out a slapstick routine.

Dating coach Alexis Germany says being funny on a date means you should just be yourself. Whether you like puns, dad jokes, or topical quips about reality TV shows, Germany urges you to show off your own sense of humor—without trying too hard.

Damona Hoffman, OkCupid dating expert and host of Dates & Mates Podcast, agrees that some non-forced humor is sure to help you connect. “Humor is the best way to ease tension on a date," she says.

So if you’re trying to break the ice or just want to jumpstart the convo on a date, here are the top 30 funny questions guaranteed to make them laugh—or at least, pretend to laugh, and then buy you a drink for trying.

1. So, you married?

If you like dry humor, asking your date something a little absurd is sure to loosen them up and get them to better understand you. “Start with what is funny to you and see if you can connect on that rather than feeling pressure to be funny,” Hoffman says. “It's about finding someone who shares and appreciates your sense of humor, not trying to entertain them like a clown.”

2. Want to guess what my passive-aggressive coworker emailed me today?

Having your partner guess what someone said to you lets them do a bit and get a little attention. It's all about the back and forth banter.

3. If I pay for drinks, can I complain about my terrible roommate clogging the sink again?

If you’ve had a shitty week, you may not be in the mood to be flirty rom-com girl happy funny. Instead of pretending you’re #live #laugh #loving life, express that you’ve had a long week in a funny way like offering to pay for drinks.

4. If someone only saw your Spotify or Netflix accounts, who would they think you are?

Asking someone to list their favorite bands/movies is tired. Rather than pressuring someone to rattle off their favorites only to pretend you’ve heard of them, ask them what their Spotify/Netflix footprint looks like. Are they secretly a 70-year-old man on vacation in the Florida Keys?

5. Would you rather be TikTok famous or win a grammy?

Germany explains that “would you rather” questions tend to lead to funny conversations. One turns into another, into another, until you’re both crying laughing. These questions are a good way to gauge what someone cares about or other interesting facts you wouldn’t otherwise learn about them.

6. What’s your best dad joke?

“Dad jokes are awkward anyway so then you can both just laugh at yourselves and have fun with it,” Germany says. “Don’t forget to prepare your joke ahead of time so you don’t freeze up on the spot.”

7. What was the first R-rated movie you ever saw? Who took you?

Asking about super specific parts of childhood is a great way to get larger insight into how someone was raised and what their family is like. Yet, making it about something silly like an R-rated movie or a song with swears in it keeps it light.

8. What’s a word you pronounced wrong your whole life?

Did you think salmon had a hard “L”? Say “parmesan” like “par-me-san”? Hoffman notes that asking about something a little embarrassing but not super emotional/traumatic keeps things light and is sure to make you bond.

9. Can you please tell me about your best worst school photo?

“Asking someone to share a funny or embarrassing moment from childhood can be a good one too,” Germany says. “The point isn’t to be a comedian but to get conversations going.”

10. What was your AIM screen name?

This is one for the Millennial crowd, you know, people who didn’t grow up on Instagram. Yet if you or your date is more TikTok than Tumblr, ask about the most embarrassing thing they’ve ever posted.

11. What was the worst middle school fashion trend you participated in?

Frosted tips? Goth pants with the chains? Tiny eyebrows? Bonus points for sharing pics.

12. What do you buy too much of but seem to never have enough of?

Chapstick? Socks? Black cherry White Claw? Ask your date about what they hoard but can never find when they need it.

13. What’s the cheesiest internet pop psychology advice that actually struck a chord with you?

Sometimes the Instagram musing of green juice drinking lifestyle influencers just hit.

14. Does being an influencer sound like heaven or hell?

Whether your date loves the Internet or still has a flip phone, asking about influencers is sure to bring some laughs and potentially open some cool conversations.

15. What’s the best WiFi name you’ve seen?

WiFi names span from cheesy to explicit. Ask them about funny ones they’ve seen, you may get some good stories about their past neighbors.

16. If your life was the “expectation, reality” meme what would the two pictures be?

Do people think you’re an extrovert but you really want to live in a small cabin in secluded woods? Asking about it in meme format is a way chiller framing of “what do people falsely assume about you?

17. If you were an amateur wrestler/D-List superhero, what would your name be?

Ask them to build an entire character, what would they wear, what would their motto be, and who is their enemy?

18. What’s your go-to karaoke song?

See, this is a test because it gauges if they 1. Like karaoke, 2. Like having fun, 3. Chose something by The Dixie Chicks.

19. What’s a book you’ve never read but pretend to have read?

Infinite Jest? The Oddessy? We all have one. Ask about their academic flexing, you may be surprised to hear about what books or classes they fell in love with in school.

20. What would your vanity license plate be?

Vanity license plates are the marriage of niche hipster cryptic internet humor and actually funny memes that your mom would laugh at. Ask them what their plate would be and prepare to howl.

21. Be honest, how many hours a day do you spend on TikTok?

Comparing screen time amounts is the new version of astrology compatibility. Ask them about their favorite pages and what first got them sucked into the ‘Tok.

22. What’s something that’s embarrassing, but shouldn’t be?

Can you recite 100 numbers of Pi? Did you dress like Avril Lavigne for all of 4th grade? Know all the words to every Imagine Dragons song? Ask them about something they do that they’re not ashamed of.

23. What type of grocery store shopper are you?

There's a big difference between a list-maker and impulse buyer. Plus, don't even get me started on the individuals who don't go up and down every aisle.

24. What’s the stupidest way you have ever hurt yourself?

If your date is naturally clumsy, you’re sure to get some good stories. Even if they’re a super balanced babe, you may hear a funny store about tripping in T-ball.

25. What was something you believed as a kid for way too long?

Did you think dishwashers were scary? The OJ and orange juice were two different things? Share your own silly memory and ask them for theirs. “Self-deprecating humor often gets a laugh because it shows self-awareness and it's relatable,” Hoffman says. “When we tap into a story from the past, we can evoke feelings of nostalgia as a bonding tool.”

26. What’s the stupidest lie you ever told as a kid?

Twisted kid logic is a guarantee to make you both laugh. Ask about the time they said their cat made a mess in the kitchen or that they were late to Chemistry class because they got lost in a forest on the way to school.

27. What is the weirdest thing about you that most people wouldn't guess from looking at you?

Maybe you sleep with socks on. Maybe you eat a banana with every meal like Camila Cabello. Asking about their quirks “cuts past the boring date script and gets to the heart of who they are and might make them giggle about it in the process,” Hoffman says.

28. How long do you wait to get up to pee when you’re watching a really good TV show?

A personal but funny question (like one about pee habits) is disarming and sure to make you both bond. If you’re not into potty talk, ask about how long it takes for them to grab the remote or go get a drink.

29. What’s the grossest food thing you’ve ever done?

Ate something off the floor? Left takeout on the table overnight then finished it in the morning? Spilling the tea on your food history will have you both giggling.