Skip to content
two girls hanging out on a sofa


Funny questions to ask a girl or guy

There are moments when a deep conversation is the way to go, but this is NOT one of those moments.

Sometimes the best way to get to know someone is through some old-school, light-hearted chat. A set of funny questions to ask – which don’t seem too scripted – will keep things upbeat. Whether it’s how to make a girl laugh over text, examples of funny questions to ask a girl or guy to initiate a conversation, or funny things to ask your girlfriend or boyfriend, relax… you’ve come to the right place.


Humor is the ultimate icebreaker, so if the conversation’s dried up, either in person or in the DMs, school yourself with these funny questions to ask. All of us should have a store of these, memorized and ready to go (but not, like, obviously memorized):

1. If someone were to play you in a romcom, who would it be and why?

As far as funny questions go, this is a safe start for when you’re trying to get to know your crush. You’re mixing romance and comedy from the word go, what’s not to like? You’ll get a good feel for their sense of humor and what they’re into depending on who they pick, which is perfect for moving on to some more funny questions to ask – you’ll know where you stand.

2. If you were the opposite gender for the day, what would you do and why?

A little bit Freaky Friday, a little bit Beyoncé belting out ‘If I were a boy’, this is one of those questions to make a girl laugh, or a guy, because it’s just a bit random. Again, prepare an answer on what you’d do if the roles were reversed.

3. Would you rather…

This format never gets old… try it, seriously. Would you rather have spaghetti for hair or eat hair spaghetti once a week for the rest of your life? The only limit is your sense of randomness. With a bit of luck, these funny questions to ask each other will escalate until you’re both crying with laughter. 

4. What’s the worst pick-up line you’ve had?

Take the pressure off yourself by throwing some shade towards the poor dudes they’ve left in their wake. This is one of those funny things to say to your crush right before you deliver your very own worst line (to show you can take it as well as dish it out, of course).



‘What would you say if I were on my way over in my chef’s hat and a box of surprise ingredients?’


When it comes to texting, the rules are slightly different. You can afford to be a little more playful. The aim of funny texting a girl or guy is to see them in real life so you can try out your lines in an actual conversation. Have a look at these top two ways (okay, so they’re not strictly questions) to make a girl laugh over text, or a guy:

1. We’ve said it before and we’ll say it again, role-play

Just launch straight in there with something zany like, ‘What would you say if I were on my way over in my chef’s hat and a box of surprise ingredients?’. Choose any scenario you like. The beauty of this is seeing how playful the two of you can get. It’s up there when it comes to funny random questions to ask a girl or guy, but it can also be a little flirty, depending on the mood you want to create.

2. Share a private joke

Through a GIF or meme (of course). Send them something that only they will get. Maybe you both saw the same film or TV show, or you live in the same neighborhood – have a think about what draws you both together – are you hipsters or hicks? – and try and find some visual media to poke fun at yourselves.



The good news? You’ve probably already done some serious wooing to make the wonderful human you call your girlfriend or boyfriend, uh, your girlfriend or boyfriend. Chances are, they already dig your sense of humor and you’ve both grown beautifully weird together. But that doesn’t mean you can’t build on your knowledge to keep things interesting:

1. What’s been our worst date and why?

Obviously, the tone here needs to be kept fun and light-hearted – assuming you’ve always had pretty great dates, they’re likely to remember something funny about one of them. The two of you can then reminisce about that weird waiter or the time you had spaghetti sauce round your mouth the entire evening

2. What were your first thoughts when I took you to meet the parents?

Another revealing question, but also likely to crack a smile and mutual laughter at the expense of your poor folks. Normally, nine times out of 10 these scenarios are pretty cringe. Maybe your dad called your girlfriend by your ex’s name, or your little brother went all starry-eyed and doused himself in your deodorant to try and impress. This is one of those funny questions to ask a girlfriend or boyfriend, because you both know each other well enough at this point to genuinely have fun and take things in good humor.

Laughter is ALWAYS the answer. Have fun with these funny questions to ask a girl or guy, regardless of whether you’re headed for that second date or not!