20 Funny Questions To Ask A Guy You Like

By on September 20, 2013

Whether you want to crack a few smiles, really get to know him or just want to play an amusing game of 20 questions, the questions put together below can truly be hilarious to ask the guy you like! You and your crush will both be smiling by the end of every answer. Here are 20 funny questions for you to ask the guy you like:

Question # 1.) What would you do if you could be invisible for one whole day?


Why It’s Funny: Knowing most men, their answers would somehow probably include them snooping around the fitting rooms of that lingerie store in the mall! Surely, you’ll get a good chuckle out of whatever he answers with.

Question #2.) What’s your favorite joke?


Why It’s Funny: Whether this joke is actually funny or not, watching him trying to put it together and try to make it funnier so that you’ll like it as much as he does- priceless.

Question #3.) If you could be a woman for one day, what would you do in that day’s time?


Why It’s Funny: This one has got to hilarious! Men don’t understand women as well as we’d like and so they are truly fascinated and equally freaked out by women, so imagine what they would do all day…

Question #4.) What is the worst thing that somebody has walked in on you doing?


Why It’s Funny: Obviously it was an embarrassing moment for a reason and usually embarrassing moments are pretty funny!

Question #5.) What is the weirdest nickname people call you?


Why It’s Funny: Whatever he finds weird about the name will probably crack you up because it’ll be silly or embarrassing.

Question #6.) Do you think you’re attractive?


Why It’s Funny: There is almost nothing funnier than watching a guy feel a tiny bit awkward about the question and then try to puff out his chest and talk overly confident about himself.

Question #7.) Can you list three words that describe yourself?


Why It’s Funny: Well, when a guy pulls out three words like, “Sexy”, “Charming”, and “Awesome” you usually get a darn good laugh about it.

Question #8.) What would people hear if they could read your mind?


Why It’s Funny: Not only guys, but usually everyone has some weird and funny thoughts that pass throughout their heads all day long… but, guys are usually way funnier!

Question #9.) What’s your dumbest pet-peeve?


Why It’s Funny: Imagine him saying something like, “When my mom tells me to put my socks away while I’m playing Call Of Duty.” Plenty of guys have really silly pet-peeves that they get super mad about and their reaction may get anyone to chuckle a little bit.

Question #10.) Who is your celebrity crush and why?


Why It’s Funny: This is a funny question to ask because a guy will usually just name off a celebrity or celebrities with the biggest… well, you know!

Question #11.) What are you afraid of the most?


Why It’s Funny: Most dudes don’t like to discuss their fears because they think it makes them look weak. So, to hear a guy actually fumble for a less weak answer is pretty funny. Or, if he is honest and says something funny like, “Kittens” or “Bunnies” you might get a laugh out of it.

Question #12.) What is your biggest turn on?


Why It’s Funny: It is pretty amusing to ask awkward questions to guys and sometimes the answer to this question can be really funny to you!

Question #13.) What is your best talent?


Why It’s Funny: Sometimes, especially if you just met this guy, he might try to over-exaggerate to make himself sound cooler to impress you. So you may hear something like, “I’m totally amazing at driving race cars. I win first place all the time!” When in reality, he probably just won the soapbox derby in 4th grade and received a blue ribbon.

Question #14.) Would you miss a sports game for me?


Why It’s Funny: Most guys are totally obsessed with sports, whether it be football, soccer, basketball… whatever… When asked he will probably get all flustered or even straight out say probably not. Come on, that’s pretty funny, right?

Question #15.) What was your most awkward sexual moment?


Why It’s Funny: I don’t think this one needs an explanation… if it was sexual and akward… it’s probably going to make you laugh.

Question #16.) What was your most embarrassing moment?


Why It’s Funny: Usually, embarrassing moments are pretty funny and even funnier when the person who was embarrassed is explaining the moment.

Question #17.) What would you do if you won the lottery?


Why It’s Funny: Guys have a completely different way of thinking than women and some of the ways that they’d spend all that money… well, it’s ridiculously hilarious.

Question #18.) If you could commit any crime and get away with it, what would it be?


Why It’s Funny: Alright, so this probably isn’t true for just any guys, but sadly, answers like, “Steal the new Madden 25 game” or “Break into Jessica Alba’s house” have been given… Ha!

Question #19.) If you could see the future, what would you hope to see yourself doing in 5 years?


Why It’s Funny: It’s always something else to hear a guy talk about how he sees himself doing in the future… if he can think that far ahead!

Question #20.) What’s your perfect girl like?


Why It’s Funny: I can hear almost any guy going, “Well she’s got to have huge….!”

Question #21.) What was your most embarrassing moment when you were in school?


Why it’s Funny: Whether it be homecoming ruses or homeroom fails, whatever story he tells will surely get the both of you giggling up a storm. Embarrassing moments are always good for a laugh! Especially coming from someone you’re into!

Question #22.) What TV show character is most like you?


Why it’s Funny: What makes this humorous is that he may compare himself to someone you would never have guessed. This might even give you an idea of how he views himself as a person. Does he really think he is as funny as that cool guy from that one show? We doubt it, ladies, but he’s cute anyways, right?

Question #23.) Do you have any cool scars?


Why it’s Funny: If he does, get him to show you! There is always an interesting story behind cool scars. Sometimes the stories behind scars are pretty ridiculous. Also, it could be in a great place… like under his shirt or on his bicep!

Question #24.) Do you think ghosts are real?


Why it’s Funny: Talks of most superstitions, myths and urban legends are always extremely goofy and fun. Does he also believe bigfoot might be real? How do you stop the laughter from flowing when touching on such an outrageous topic.

Question #25.) What’s your favorite comedy movie?


Why it’s Funny: The word comedy is right in the question itself on this one. Your man will surely crack a smile or two while he tells you about his favorite funny film. You may both even enjoy the same movies, but more than likely he may resort to the typical guy flicks, you will only find out if you ask!

Question #26.) How would you spend a week if you could do anything you wanted?


Why it’s Funny: The answer to this question may give you a look at how frivolous he can be. Would he spend a whole week eating Doritos playing the newest Xbox game in his underwear? Maybe he’d mess around with his friends… Or maybe he would spend all the extra time with you. Something in his answer whether silly or serious will encourage a few smiles.

Question #27.) Who is your funniest friend?


Why it’s Funny: Everyone starts to light up when they talk about their favorite friends. Asking him who his funniest friend is will definitely get him to open up and hopefully tell a few hilarious tales.

Question #28.) Do you like being tickled?


Why it’s Funny: Prepare yourself for some playful teasing! Asking him this may give you the opportunity to get a little closer to him.

Question #29.) Are you afraid of anything silly?


Why it’s Funny: Is he afraid of something outrageous like balloons? Get to know what really freaks him out. It could be an absolute riot just seeing how silly his answers can get!

Question #30.) What’s your favorite pickup line?

Why it’s Funny: Pick up lines are always corny, aren’t they? How could you not laugh? Or maybe the guy you like will sound pretty darn good while he is saying it…


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