The same old small-talk questions might get old. But, you definitely want to make sure to ask questions, as many men sometimes fail to do so can steer you towards bad date territory.
If you’re struggling to keep a conversation going, or just want to add some comic relief to the flirtation, here are 50+ funny questions to ask a girl to make her laugh.
The Top 50 Funny Questions to Ask a Girl to Make Her Laugh
- If you woke up invisible tomorrow, what’s the first thing you’d do?
Hopefully she doesn’t say, “go through your phone.”
- What’s your weirdest deal breaker?
- What’s the worst date you’ve ever been on?
Take notes here, too.
- What’s the best Halloween costume you’ve ever worn?
The answer to this question may also include a photo.
- What cartoon do you still like to watch?
You be the judge of whether adult cartoons (Family Guy, Simpsons, etc.) count or not.
- What’s your go-to drunk and/or hangover food?
Make sure to find out if your date drinks before asking this question.
- Who’s the first celebrity crush you’ve ever had?
Yes, cartoon characters count.
- What’s your zodiac sign and do you think it’s accurate?
Even if neither of you believe in horoscope, this is a fun way to learn more about your date.
- Which fictional place would you love to visit?
Think Whoville, Narnia, Hogwarts, Willy Wonka’s Chocolate Factory, and the like.
- What’s a funny nickname from your past?
Like with most of these questions, be prepared to answer for yourself too!
- Would you rather have more money or more time?
This may not be funny per se, but it’s definitely interesting and could lead to a great conversation.
- What’s your go-to karaoke song?
Store this information for later.
- What’s the last meme you screenshotted?
Make sure to give her privacy when scrolling through her camera roll.
- What’s the worst job you’ve ever had?
Maybe you’ll get a funny story about her scooping ice cream for bratty kids or actually having to save someone as a teen lifeguard.
- If you were arrested and your family found out, what would they assume you had done?
Hopefully she doesn’t say murder!
- If your pet could talk, what do you think they’d say?
For obvious reasons, only ask this one if you know your date has a furry friend.
- When’s the last time you found yourself in a food coma?
This is a good way to potentially find out her favorite food for your next date.
- What fashion trend from the past did you refuse to participate in?
Ponchos? Low-rise jeans? Frosted tips?
- What fashion trend from the past do you regret participating in?
Photos or it didn’t happen.
- What song is your guilty pleasure as of late?
We all have one (or many).
- If your internal monologue suddenly became audible, how screwed would you be?
Dive deep into your date’s mindset.
- Would you be more or less likely to talk to me if I grew out my hair and put it in a man bun?
This is a cheeky way to find out more about your date’s taste in men.
- Would you be more or less likely to talk to me if I wore a gold chain?
Same as above.
- What’s the funniest conversation you’ve overheard?
If you live somewhere that has an “overheard page” (example: @overheardLA), you can ask her if she knows about that page and if she’s ever heard anything worthy of submission. Bonus points if you’ve seen something funny on the page that you can also share.
- If you were an animal, which would you be and why?
Or, ask her what animal you look like!
- What alcoholic beverage brings back bad memories?
Read the room and make sure you ask this in a lighthearted way. You’re aiming for a response like, “I can’t have vanilla Smirnoff because it’s all I drank freshman year of college.”
- Do you say “yes” or “no” more often in life?
This is a great way to learn more about a person, because hopefully they’ll explain their answer. And if they don’t, ask them to!
- If you could be a character on the last show you binge-watched, who would you be?
This is one of the funny questions to ask a girl to make her laugh that takes a standard first-date question and makes it a little more fun.
- What’s an incorrect assumption many people make about you?
This gives your date a chance to clear up any confusion and put her best foot forward.
- What’s an invention that you think they should’ve come up with by now?
Flying cars, time machines, those microwaveable meals from Spy Kids. The possibilities are endless.
- If you had your own cooking show, what would you make?
Feel free to take her answer, put on your best announcer voice, and act like you’re narrating her cooking show for her.
- If you were a man for a day, what’s the first thing you’d do?
This could lead to some interesting responses…
- What’s an unconventional trait that you find really sexy on a man?
Maybe she loves bald dudes or guys with eyebrow piercings? Or maybe she just is a sucker for a guy in a bow-tie. These are all great things for you to know.
- If you had to smell like a food for your entire life, which would you choose?
This is another great way to potentially find out her favorite foods.
- What’s the last thing you burst out laughing at?
If anything, this will give you a window into her sense of humor and let you know why she might not be laughing at your jokes yet.
- What’s something about me that you think is funny?
Women can be sassy, so don’t ask this if you’re not prepared to take it.
- When did you find out that Santa Claus wasn’t real?
This question is best asked around the holiday season to not appear super random.
- Would you eat worms for $1000?
Feel free to sub in worms for any somewhat-gross item nearby if you’re on a date.
- If you were on Jeopardy, which category would you excel at?
Here’s a way to get your date to show off what random facts she knows best.
- If you could be on any reality show or game show, which would you have the best chance at winning?
If she says Too Hot Too Handle, make sure to take things slow with her.
- Can you wink?
This is a question that should be asked in person so that you can both practice your best wink.
- Can you raise one eyebrow?
Similar to the above question, this makes for a silly activity on a date.
- What’s your most used emoji?
You’d be surprised how much you can tell about someone from their emoji usage.
- What’s the weirdest celebrity encounter you’ve had?
This can lead to a funny story, or let you know that your date was a 1D fangirl in a past life.
- If they were to make a movie about your life, what genre would it be?
Hopefully she doesn’t say horror.
- Did you have any posters of singers or bands in your room as a teen?
This is one of the funny questions to ask a girl that is way more exciting than, “what kind of music do you like?”
- Have you ever performed in a talent show?
A great way to find out if your date has any secret talents or is super shy.
- What’s your favorite form of potatoes?
This question works best when ordering off a menu that includes french fries.
- What’s something that’s always in your fridge?
We all know what a typical bachelor fridge looks like, but what about a bachelorette’s fridge?
Keep in mind that if you’re using these funny questions to ask a girl to make her laugh, you want to try to work them into a conversation. If you text her out of the blue with a question, it might seem a little random and disingenuous. Instead, try to work in an animal question when she’s already talking about her dog. Or, try question #26 after you’ve both ordered drinks at the bar.