66 Flirty, Naughty & Funny Questions to Ask a Girl & Leave Her Tingly

The best way to get a girl to notice you is to use your sense of humor. Try these funny questions to ask a girl and watch how she hangs on your every word!

Delivering a line that leaves a woman laughing all the way home is not an easy task. You could go for a couple of tried-and-tested jokes but this approach, unfortunately, can sometimes be too much. You don’t need to launch into a whole stand-up comedy routine, but learning a few funny questions to ask a girl will help you ease your way in.

Another alternative is the cheesy one-liner. You know the kind of thing: how do you like your eggs in the morning? Did it hurt when you fell out of heaven? If I said you had a beautiful body, would you hold it against me?

However, cheesy lines can make you seem a bit archaic and pathetic to some women, and may have entirely the opposite of the intended effect. Why not try a different strategy this time?

Coming up with funny questions to ask a girl you like can be a little challenging, especially if you aren’t prepared. Find out here when would be the right time to ask, how often, and what to say. [Read: 70 hilarious cheesy pick up lines to get a girl laughing]

What should I do then?

The best approach to get a woman rolling on the floor laughing, without needing to sacrifice your dignity, is to hand the baton to her. Ask her a question that will have her reliving humorous experiences or putting herself in humorous hypothetical situations, and let her discover the laughter herself.

Not only do you automatically appeal to her personal sense of humor, but it’s also a less egotistical and more inclusive way of getting her on board. Not to mention the fact you will get to know her more based on her answers, and naturally form a bond with her.

Take your time thinking about what funny questions to ask a girl, and observing whether she’s in a good mood or not. Doing so will help save you from future embarrassment. [Read: Questions to ask a girl to get to know her better – 35 ways to her heart]

How to ask a girl funny questions

You might be wondering how you can fit these questions into a conversation. Obviously, don’t throw them at her like she’s in a job interview. Pepper them throughout your chat and look for the right moment to slot a funny or flirty question in.

It sounds so obvious to say, but you’ll know the moment when it arises. If there’s a lull in the conversation, that’s the ideal time too.

Ask the question with a cheeky grin on your face or a wink, and she’ll feel totally at ease and in the right frame of mind for some witty back-and-forth banter!

If it’s a flirty question you’re posing, the wink is definitely a good move to accompany your question. [Read: How to flirt with girls – 25 secrets & 41 lines to seduce and make her blush]

Funny questions to ask a girl

To help you on your way, we’ve included a list of the best questions most likely to initiate the ROFL effect. We’ll even throw in some flirty questions to ask a girl too, just to give you a full-rounded effect!

1. Would you describe yourself as naughty or nice?

This one is bound to get her thinking and won’t really press her to feel the humor until you insist on her justifying the answer. Then the giggles will make a sudden and welcome appearance.

But when she does finally give you the answer, be careful how you react, or you’ll offend her. There’s a reason why you asked her that, and the last thing you want to do is make her feel bad about herself when she describes herself as naughty or nice. [Read: Are good looking girls mean or nice?]

2. What would you do if you could be invisible for one day?

You can imagine some of the answers you might get to this question — nearly all of them hilarious. A funny question with definite ROFL potential. This is one of the most unique in our list of funny questions to ask a girl you like.

3. What is your most embarrassing sexual moment?

Embarrassment is nearly always funny *even when it’s your own* as long as it’s told in the right environment. Then it just becomes hilarious and something to be shared and enjoyed. You’ll also have the chance to get to know her views on sensitive topics like this one.

Depending on your level of closeness or friendship, she’ll give you a straightforward answer or dodge. Regardless of what her response is going to be, asking a girl funny questions is always a good way to know her better. [Read: 15 painfully embarrassing things that happen during sex]

4. What’s the funniest thing that’s ever happened to you?

The clue’s in the question. If it’s the funniest thing she’s ever experienced, then it obviously has the potential to re-amuse at will. And you’ll be right there to share the frivolity with her.

If she talks about the most embarrassing, yet funniest moments in her college life, listen and laugh with her. There’s a reason why she talked about those moments and that is because she’s comfortable around you. That’s a plus point, so make sure to include this in your list of flirty and funny questions to ask a girl you like.

5. What’s the weirdest nickname you’ve ever had?

You have to be in a position of trust to ask this one, and if you are, the embarrassment factor can deliver very funny results. Sharing your nicknames with a friend or with strangers means a lot. Don’t be too surprised when she quickly gives you the answer!

It could mean that she always loved to be called by that nickname or simply, she wanted to share her nickname with you because she’s comfortable with you. Sounds cool, right? Give it a try next time. [Read: Cute pet names for couples and how to pick nicknames for each other]

6. What’s the weirdest crush you’ve ever had?

Everyone has a funny story about some former puppy-dog crush, and an embarrassment reciprocated can lead to laughter all around. We all experienced those “puppy love” days, especially back in high school.

Why don’t you ask a girl you like this question and observe her reaction? It may tell you whether she still has a crush on that guy or not. It won’t hurt to try! If you want to get to know her past relationships or crushes, you should definitely include this in your ‘funny questions to ask a girl’ list. [Read: How your first love affects your future relationships]

7. Who would you do between…?

A choice question. Choose three of the most objectionable individuals you can imagine and then ask: if she had to have sex with one of them, who would it be?

Ask her to justify their answers to add to the laughter. You could even go for specifics, and name celebrities for her to choose between.

This also falls into the ‘flirty questions to ask a girl’ category. [Read: 100 juicy, random, funny questions for flirty guys and girls]

8. What are the best and worst things about being a woman?

Expect some flak for this one – being a male of the species. But that’s half the fun! Let her unload on you and take it on the chin, showing her that you are a real man who can enjoy a laugh at his own expense.

9. If I caught you masturbating, would you carry on, or stop and pretend you weren’t?

An extremely embarrassing question leading to hilarious answers and a lot of fun all around. Quite saucy too. At first, she might laugh. Of course! But be prepared, as well, if she doesn’t give you an answer to this one.

However, this one might also make her feel uncomfortable if she’s not ready to talk about sexual stuff with you yet. However, you could still include this in the list of more risqué questions to ask a girl you like. [Read: How to masturbate – 23 self-pleasure and solo orgasm secrets for girls]

10. What’s your favorite joke?

Again, the clue’s in the question. It’s her favorite joke, so it is bound to get her laughing. Even if it’s terrible, it can become a source of amusement in itself.

We’ve all heard tons of jokes in our lives, but remembering one specific joke that made us laugh out loud is different. [Read: How to be funny – 28 must-know tips to make everyone love your humor]

11. What’s the habit you hate most in a boyfriend?

She will no doubt have some anecdote to hand about a former boyfriend that she can bring to the conversation — and as we all know, former horrors are amusing tales in the future telling.

If you feel that this question might be sensitive on her part, consider thinking of other questions to ask instead.

Always have a backup! But if she answers you in a straightforward manner, ask her a follow-up question, like “why?”. Soon you’ll realize the conversation is getting deeper as you go along, and it’s a good thing. [Read: 40 questions to ask your crush and subtly flirt with them]

12. What’s the first thing you’d look at if you saw me naked?

She’ll roar with laughter at this one, and it will encourage her to be creative with her answer. Always a good way of getting the laughter flowing. As a guy, what answer are you looking for?

But what if you didn’t get the answer you were hoping to hear from her? How would you react? Coming up with funny questions to ask a girl, like this one, can be awkward for both of you at first.

13. What’s the worst thing someone has walked in on you doing?

She will probably fight you on this one to begin with, but once she eventually opens up, you’ll both be roaring with laughter.

It might even lead to a flirty conversation if the thing she was doing when the person walked in was a little risqué! [Read: How to act cool in front of a girl and banish the awkwardness]

14. If people could read your mind, what would they usually hear?

You’ll encourage her creative side to flow freely with this question, and it could range from the mildly embarrassing to the rip-roaringly offensive. If you’re thinking about funny questions to ask a girl you like, you can start safely with this.

15. What’s the wildest sexual fantasy you’ve ever had?

A very naughty question, and one that could also be very funny too.

Asking this question will only work for those people who are already close enough, don’t you agree? So if you and the girl you like are just starting out as friends, it’s not a good idea to ask about her wildest sexual fantasy.

Remember that not all girls are born the same. Before you start asking her very personal questions, take your time to get to know her properly. [Read: The most arousing sex fantasies worth trying in real life]

16. Would you rather be beautiful and dumb or ugly and clever?

No matter what the answer, there’s great potential for fun, in addition to a well-placed compliment or two. In fact, this question has been going around for decades, and we all know some famous answers to it.

While many girls would prefer the “ugly and clever,” some might say, “I’d choose to be dumb but beautiful, because I’d still have the ability to improve, learn, and grow myself with knowledge as much as I can.”

Her answer could be very interesting indeed. [Read: 134 smart and funny ‘would you rather’ questions leave you ROFL]

17. Which sexual kink would you be least likely to try?

You could both get really creative and silly on this one – depending on what kind of sense of humor you have – and be ROFL for the rest of the evening. This is one of the most flirty questions to ask a girl because it moves into sexual territory.

If you and the girl you like are just beginning your friendship, it’s best not to attempt to ask this ridiculous question. However, if your relationship with her is getting stronger each day, asking this question is acceptable.

18. Have you ever been caught naked by someone you didn’t want to?

We all have, and it’s always funny in the retelling — no matter how horrifyingly embarrassing at the time. When you ask her this question, she will probably reminisce about her childhood or teenage years.

The only possibility of someone seeing you naked back then was when you were at home, inside your room, getting dressed for school. Perhaps your mom opened the door suddenly and saw you naked. Yep, her too; this could easily be one of the situations she’s going to tell you about. [Read: How to get a girl horny and wet just by sitting next to her]

19. If you could be a guy for just one day, what would you do?

Probably more than any other question on this list of funny questions to ask a girl you like, this one has the potential for so much hilarity you’d be a fool to leave it out. To be honest, there are lots of women who think about this situation happening in real life.

20. Do you think you’d know if I was feeling horny?

This is a kind of poking-fun-at-yourself question. Women are quite proud of their intuition on such things, and find men’s equivalent crassness quite funny. Again, asking this to a girl you like still depends on your level of closeness or friendship.

The goal here is to make her laugh, not to make her feel uncomfortable. Beware of what you say.

Always think before you open your mouth, or you’ll end up with a black eye! But again, this is definitely one of the best risqué questions to ask a girl you’re into. [Read: How to tell if a guy has a boner – 20 signs and turn-ons to get him hard]

21. What was the last crazy adventure you went on?

Want to discover how daring she is? This is the question you should ask her. When you have a more adventurous lady on your hands, you can be more direct in your communication, which may result in your relationship developing more swiftly.

On the other hand, if she is more conservative, you should move gently and gradually with your plans. [Read: 50 relationship questions to test your compatibility instantly!]

22. What’s the most valuable thing in your life?

You’ll find out what she considers to be the essential things in life. While you don’t want to assume things about her whole personality based on one question, if the item in question is a tangible object, you may find she is more materialistic than other ladies.

If it’s her cat, you can be sure she’s an avid animal lover. You get the gist of it. Even if this does not fall under the category of funny questions to ask a girl you like, it’s still worth giving it a chance.

23. If you could live anywhere in the world, where would it be?

The environment you live in has a significant impact on the life you lead. Her response to this question will provide you with a better understanding of how content she is with her current living situation and what sort of environment she would want to be in.

Is it a good match for your lifestyle? Make sure to share yours as well. When you talk about the future with a girl, she is forced to imagine you as a part of her future. Isn’t that a cool trick? [Read: 15 reasons why you should travel at least once a year]

24. If you found out I slept with a stuffed animal at night, what would you do?

Asking this question to a girl you like can be a little bit awkward, but it’s satisfying to witness their true reactions. Some girls might think “what a weirdo!” Some might think “aww, how cute!” It really depends!

But giving this one a go will surely have her laughing and that’s enough. Finding out her answer is not the goal here, but rather finding out how to make her laugh.

25. What are you most passionate about right now?

Have you ever said something that made somebody’s whole face light up when you’re talking to them? We’re confident that you have. Almost certainly, you’ve stumbled upon something they’re passionate about.

She will always associate positive feelings with you if you are the one who persuades her to talk about the topics that she is most passionate about. [Read: 60 deep & fun get to know you questions to peek into their soul!]

26. Would you rather be able to play multiple musical instruments or speak many languages?

This is an interesting question to ask because it tells you a lot about what is important to her. If she says musical instruments, it tells you she’s a creative soul. If she says languages, maybe she’s someone who wants to see the world.

27. What vegetable would you prefer to be?

Obviously, nobody really wants to turn into a root vegetable, but if she had to, what would it be? This is one of the funny questions to ask a girl that will no doubt make her laugh from the get-go. But make sure you probe a little further and find out why she chose that vegetable!

28. Which one, an infinite amount of time or an infinite amount of money?

Nobody will be able to answer this question easily, and she’s likely to take a moment to think about it. It could bring about a really deep conversation however, so be sure to figure out what your answer would be too.

29. Let’s talk deal breakers – what is your weirdest one?

It’s interesting to find out what a girl’s deal breakers and red lines are, and some weird ones are sure to come up. Remember, these conversations should flow back and forth, so when asking funny questions, you need to have your own answer prepared.

30. If you had to smell like one particular food forever more, which would it be?

Will she choose chocolate? How about ice cream? Maybe she’ll throw you a curve-ball and say chips!

31. What are your biggest and strangest goals in life?

Some of these funny questions to ask a girl may not seem humorous at first, but you have to think of their potential to go to funny places. If she has strange goals, that could bring about a laugh or two!

32. What’s the craziest thing you’ve done on the spur of the moment?

You’ll get to find out if she’s an adventurous, spontaneous girl or someone who always thinks before she acts. The answer might also be hilarious! [Read: 18 ways to become more spontaneous in life]

33. What’s the worst pick-up line you’ve ever had to endure?

Every girl has heard their fair share of dodgy pick-up lines in their time and they do cause mass hilarity when reciting them back. Take note of what she says, and be sure to never use them yourself!

34. What is your weirdest pet peeve?

This is useful because you know to avoid it at all costs! We all have things that get on our nerves and sometimes they’re the downright strangest things.

What are yours? Let her know so she can avoid those too!

35. Cereal is a soup – yes or no?

Believe it or not, some people actually think that cereal is akin to soup. Is she one of those people? Are you? It’s interesting to find out! [Read: Weird trends millennials have to explain to their kids]

Now let’s move into the flirty questions to ask a girl! We’ve covered a few so far, but these are definitely more flirty than funny.

36. What did you think when you first saw me?

This will clear up any misunderstandings you may have had. If you’re not sure if she is into you, ask this question. You may not like what she says, but you’ll at least get an answer.

If she doesn’t respond… well… now you know.

37. When was the last time you had a wet dream?

Maybe she remembers the first time she had a wet dream. She may be nervous to answer this question, so if you answer first, you’ll break down the barrier. [Read: How to have a wet dream – 15 ways to hot sex dreams and sleep orgasms]

38. Where’s your favorite place to be kissed?

You don’t have to re-enact her answer, but it’s not a bad idea to keep it in mind for possible future encounters!

39. What’s your biggest turn-on?

This is a great question to see what she’s into and if you are sexually compatible. Whatever she says, remember her answer. This will come in handy for later, trust us.

Plus, if she notices that you were listening, you’ll score even more brownie points. [Read: 36 racy, random funny questions for flirty guys and girls]

40. What’s your biggest turn-off?

Just like the “turn-on” question, this is one of those flirty questions to ask a girl where the answer plays a big part in whether your potential future sex life is going to be fun or not.

Even if you’re going to have selective hearing on the rest, at least pay attention to this answer.

41. What do you wear to bed?

Maybe she sleeps nude? Well, you’ll never know until you ask. Plus, it’ll probably leave you with a nice image in your mind if she says that she sleeps naked or only with underwear on. [Read: 20 dirty questions to ask a girl and leave her wet]

42. Who do you think should make the first move – the guy or the girl?

Does she like being in control or does she like the man to take the reins? Maybe she likes to take charge, and in that case, you have it easy!

43. What three words describe you?

This is a great way to see who she thinks she is, and what she considers her important qualities to be. Not only that, but you’ll be able to see whether she describes personality traits or physical characteristics.

44. Have you ever tried friends with benefits?

Find out if she’s engaged in any open relationships. You can also see if she’s remained friends with her friends with benefits.

This is a good way to see how she handles relationships that were just based on friendship – and ones based on sex. [Read: How to make a girl want you and desire you sexually]

45. Do you like dirty talk?

How do you know if you can talk dirty to her if you don’t ask? This is a great question to see what her boundaries are in the bedroom. For that reason, it’s one of the best flirty questions to ask a girl.

46. Where is the most public place you’ve had sex?

Perhaps she likes having sex in public, or maybe she’s more of a private person. It’s a good way to see how kinky she is and if she’s willing to try things out. [Read: 20 make-or-break freaky questions to ask a girl]

47. Have you ever tried a sex toy?

If she has, then she won’t hesitate to bring it into the bedroom. If you’ve used sex toys and she hasn’t, this would be a good opportunity to ask her if she’s curious about trying.

If she is, well, now you’ll be able to bring that into the bedroom.

48. Do you like cuddling in bed?

It’s always good to know if you’ll be having a numb arm or not. If you like cuddling and she likes cuddling – great! [Read: How to cuddle with a girl so it leads to sex every single time]

49. Have you ever kissed a girl before?

Well… has she? If so, ask her if she enjoyed it and would do it again. Maybe she’s interested in exploring her sexuality with you. This is one of the flirty questions to ask a girl that could take things to a whole other level.

50. Boxers or briefs?

We know this may seem like a silly question, but why not know what turns her on? Flirty questions like this will help her envision you without your clothes on.

51. What’s your ideal romantic date?

Pay close attention to this answer and see what she’s really looking for. Maybe she’ll say skydiving or snorkeling, or maybe she’ll say a picnic along the riverside.

Whatever the answer, you’ll be able to see what she’s into and what she’s looking for in a relationship. [Read: 33 awesome date ideas every couple should try]

52. What do you think is my best feature?

See what turns her on about you. Maybe it’s your smile or your sense of humor that lures her.

53. Have you ever had a naughty dream about me?

Yessss, this is a great question to ask. If she says yes, then ask her what the dream was about.

See if maybe you can re-enact it for her. You know, to make her dreams come true.

54. What is your favorite part of a man’s body?

All women have an answer to this question. Strong arms, firm jawline? She’ll have a couple of body parts on her list. [Read: The subtle moves to seduce any girl and get her in bed]

55. Would you ever have a sugar daddy?

Does she like the idea of a sugar daddy? Is she into having a guy buy expensive things for her and take her out to fancy restaurants in exchange for sex? It’s a good way to see what she values in life and how far she’s willing to go for material possessions.

56. Have you ever had an orgasm?

Now, this is a crucial question. Maybe she’s never had an orgasm. If not, well, it’s your job to give her one! If she has, then ask her what makes her orgasm.

57. Do you want me to kiss you?

This is one of the best flirty questions to ask a girl that will initiate action! If she’s interested in you, she’ll say ‘yes.’ This is basically the golden ticket – so use it when the moment is right. [Read: 7 big signs a girl gives away if she wants to sleep with you]

58. Do you believe in love at first sight?

This could sound cheesy, so remember to throw in that wink or grin when you ask. Does she believe in the Disney fairytale or is she more pragmatic?

59. If I suggested we head off somewhere right this second, where would you choose?

Not only is this one of the flirty questions to ask a girl to find out what she likes, but she might actually say ‘come on, let’s go!’ You never know! It might turn into an actual date without you even planning on it.

60. What is the one thing you like about yourself the most?

While nobody really likes to admit it, we all have one thing we quite like about ourselves. Sometimes you have to dig a little deeper to find it, but she’s sure to have one or two things she admires.

You could take the flirting up a notch by saying that you agree with her, or coming up with a few different qualities to add. [Read: How to build self-confidence – 16 ways to realize you’re worth it]

61. Why should I take a chance on you?

Oh, you’re going in with confidence! Remember to grin and wink with this one because otherwise, it could come over as rather arrogant. However, if you time it right and let her know you’re joking, she’ll not only laugh but probably tell you why she’s a great catch too.

62. If you had to give up a relationship for one food, what would it be?

Is she a chocolate lover who would do anything for a block of her favorite? Or is she all about gourmet food, and would throw you out of her house just so she could enjoy takeout from her favorite restaurant?

Hopefully, there is no food she would give up a relationship with you for, but she might come up with something interesting! [Read: 30 hot, sizzling ways to spice up your sex life and leave you horny 24/7]

63. What is the number one sexiest thing a partner can do to you?

What does she find super-sexy that gets her all hot and bothered? Take note here and make sure that at some point, you actually do it!

64. How should I try to charm you?

Let’s be honest, sometimes, you just have to come right out and ask what you should do. In this case, go for it! She might find it endearing that you’ve asked, or start to laugh. Either option gets the job done!

This is one of the flirty questions to ask a girl that will get major results!

65. When you’re alone, what do you like to do the most?

If you want to turn this into one of the flirty questions to ask a girl, just accompany it with a grin or a wink. She might get the hint and tell you exactly what she likes to do!

But she might also tell you other things too, which can help you get to know her. [Read: Alone time – why you need it, how it helps, and how to make the most of it]

66. Is that blush because of me?

She’s going to blush even more, for sure, but she will probably laugh too! You’re flirting here, but you’re showing your sense of humor too, and that’s the single best way to charm her.

This is one of the best flirty questions to ask a girl, because it leaves her in no doubt that you are actually flirting!

Humor helps improve our relationships with our partners

Nothing helps life run more smoothly than a good sense of humor, and it’s vital in our romantic relationships too. The capacity to make someone laugh is one of the most sought-after qualities in a partner.

The best way to start things off is to come up with funny questions to ask a girl you love, and then take it a step further and get a little flirty!

[Read: How to make a girl laugh, smile and fall for you instantly]

Now you’re armed and ready with these funny questions to ask a girl, you can get her ROFL all night long and falling straight into your arms—or, if you’re really lucky, into your bed!