Random fun questions to ask a guy

200 Funny questions to ask a guy to make him laugh and ignite a fun, flirty and interesting conversation.

Getting to know a guy you like’s sense of humour is an important part of the dating and courting process. While yes, you should definitely ask some serious questions to see what his intentions are. It’s also important to keep things fun and flirty and hopefully see if the sparks start to fly between you. 

One good way to do this is to ask him funny questions. Which can lead to a playful conversation that leaves you both laughing and enjoying yourselves. And even though the questions are meant to be fun, it doesn’t mean that they can’t also reveal a lot about a guy.

For example a flirty question with a playful twist about his funny, weird or cool past experiences. Or personal opinions by way of silly would you rather type questions. Even a fun question that references pop culture can reveal a lot about his likes and dislikes. Thus helping you to see some of the things you do or don’t have in common.

Take your conversation to the next level when you ask him one of these 200 funny questions to ask a guy. Make him laugh and see if the sparks fly. Below you’ll find questions that are fun, cool, interesting, random, funny yet deep and flirty. There are also questions that you can text a guy, ask him in person or online. Which are good for those much needed conversations starters on dating apps like Bumble, Tinder and Hinge.

1. If your life was the “expectation vs. reality” meme what would the two pictures be?
2. Do you consider yourself more of a nice person or a naughty person?
3. What’s the weirdest thing you’ve given someone as a gift?
4. Would you rather make your internet search history public or your bank balance?
5. What do you think will finally break the internet?
6. What’s the most embarrassing thing you’ve ever done to get a crush’s attention?
7. What’s your favorite snack besides me?
8. If you came with a warning label, what would it say?
9. What’s the most awkward thing that’s ever happened to you on a date?

1. What’s something that people think makes them look cool, but actually makes them look ridiculous?
2. What’s your most embarrassing childhood memory?
3. What’s the worst thing your parents have ever caught you doing?
4. What are you too old to do but still enjoy doing?
5. What is the worst fashion trend you’ve ever taken part in?
6. What’s the first thing you wash in the shower?
7. Why do men have nipples?
8. What’s the weirdest thing you’ve ever done at someone else’s house?
9. What’s the dumbest rule you’ve ever been forced to follow?
10. How long do you think you would last in the Hunger Games?
11. What’s the most awkward thing that happens to you on a regular basis?

Funny Questions to Ask a Guy You Like

If you’re looking for some fun questions to ask a guy that you like then we’ve got you covered! Below you’ll find some good questions to get to know him that are funny. Keep the conversation flowing and you both laughing. All while deepening your connection as you enjoy getting to know each other a bit better.

1. What’s a totally terrible movie that you absolutely love?
2. What’s the weirdest app you have on your phone?
3. What’s the weirdest crush you’ve ever had?
4. Which Hogwarts house would the Sorting Hat most likely put you in?
5. What is the weirdest nickname people have ever called you?
6. Would you rather be able to only whisper or only shout everything?
7. If you could pick any celebrity to officiate your future wedding, who would it be?
8. You are about to kick some serious butt, what song comes on as your soundtrack?
9. What is something that everyone looks stupid doing?
10. Would you rather always have to say everything on your mind, or never speak again?
11. Would you rather have bionic arms or bionic legs?
12. Do you believe in any conspiracy theories?

1. What’s the craziest thing you’ve done on a dare?
2. What job doesn’t exist but should?
3. What fictional friend group would you like to join?
4. If I say “sexy”, what is the first thing that you think of?
5. If you were a superhero, what kind of secret identity would you have?
6. What would be the creepiest thing you could say while passing by a stranger on the street?
7. What did you think was silly until you tried it?
8. What is the worst lie you’ve ever told your parents?
9. What is something that I wouldn’t believe about you?

Funny Random Questions To Ask A Guy

Funny random questions can put a cool twist on an otherwise dull conversation. Catch him by surprise by asking him one of these questions that are both random and funny.

1. Would you rather dance a jig in front of people or dance naked alone?
2. Who is your celebrity doppelgänger?
3. If you could marry any fictional character, who would it be?
4. What would you do if you could become invisible for a day?
5. If you were famous, what stage name would you use?
6. What would your vanity license plate be?
7. What is something that is really popular now, but in 10 years everyone will look back on and be embarrassed by?
8. What’s the best WiFi name you’ve seen?
9. If your life was a podcast, which one would it be?
10. Which mythical creature do you wish was actually real?
11. If you were a wrestler, what would your signature move be?
12. What is the sexiest vegetable?
13. What’s the one superpower that you wish you had?
14. What is the funniest dream that you had that you can recall?
15. Has anyone ever walked in on you naked?
16. What was your first-ever email address or screen name?
17. Would you rather eat jalapeños with every meal for the rest of your life or a raw egg every morning?
18. What’s your go-to lie when playing “two truths or a lie”?
19. What is the weirdest thing you’ve had in the fridge?
20. What’s something that you are weirdly competitive about?

Best Funny Questions To Ask A Guy

The best funny questions to ask a guy can be a gateway to learning something interesting about your love interest while keeping things light and flirty. Below you’ll find a list of good fun questions to ask him to get your conversation started.

1. What high level job do you think you could lie your way into with no experience and no one would notice?
2. Would you rather go on a date with someone who does cheesy magic tricks the entire time, or go on a date with someone who tries to sell you the beach body protein shakes at the end of the date?
3. If you could have any foreign accent, which one would you pick?
4. If you could dip anything into chocolate and eat it, what would it be?
5. What do you think would be the worst “buy one, get one free” sale of all time?
6. People who don’t return grocery carts: heroes or villains?
7. What do you think is the best way to prepare for a zombie takeover?
8. Wanna play two, truths and a lie? Tell me three things about yourself right now, and I will guess which two are total lies.

1. Would you rather have Joe Exotic’s haircut from “Tiger King” or Edna Mode’s haircut from “The Incredibles”?
2. What secret conspiracy would you like to start?
3. Have you ever been caught singing when you thought no one was listening?
4. What’s one show, movie, or book, you’re embarrassed to admit you enjoy?
5. Would you rather only be able to speak in rhyme for an entire first date (without offering explanation), or have to recite the Pledge of Allegiance before each bite?
6. Just heading out for a girl’s night….Drunk-text you later?
7. What’s your most embarrassing hidden talent?
8. What’s the funniest movie line you’ve ever heard?
9. What is the weirdest thing you have seen in someone’s house?
10. What’s the weirdest piece of trivia that you know?

Funny Questions To Ask A Guy To Get To Know Him

Everyone knows that starting a game of 21 questions can set the tone for a fun conversation. Below you’ll find 21 funny questions to ask a guy so you can get to know him better and both have a good laugh together!

1. What was something you believed as a kid for way too long?
2. Plan your dream birthday. Where are we going, what kind of cake are we eating, and what present am I getting you?
3. What’s one thing you wish we knew five years ago?
4. Would you rather be funny, smart or sexy?
5. What was your childhood nickname?
6. What was the random compliment that someone gave you that really got stuck in your memory?
7. What’s a fashion trend you used to rock but now totally regret?
8. What’s the worst thing you’ve ever eaten?
9. What is your signature dance move?
10. What flavor combination is kind of weird but you really like it?
11. If you could be a pop icon, who would you be and why?
12. What part of a kids’ movie scarred you for life?
13. Have you ever skinny dipped?
14. If you were given the chance to marry any fictional character, who would it be?
15. What’s the most absurd thing that has become a reality for you?
16. What’s the weirdest thing about you?
17. What’s one thing that never fails to make you cringe?
18. What is a food most people love that you hate?
19. What song do you have to sing along with when you hear it?
20. What social convention do you find the most annoying?
21. Which fictional character do you identify with the most?

Funny Questions To Ask A Guy Over Text

20 funny questions that you can text a guy. Because these days you can never have to many questions on hand of funny things to text a guy to make him laugh. These text messages can also double as good questions to ask online. Or on dating apps such as Bumble, Tinder, Match or Hinge.

1. What would you do if you met your own double?
2. Have you ever texted a spicy photo to the wrong person?
3. Do you also still think about all the embarrassing things you said in middle school, or are you a well-adjusted adult?
4. Would you rather only Netflix or only chill for the rest of your life?
5. What’s the weirdest celebrity crush you’ve ever had?
6. Which celebrity’s life would make the most insanely “so bad it’s good” reality show?
7. Have you ever had a racy dream about me?
8. What do you think my superpower is?
9. You are can choose only one – You are kinda dumb but happy all the time or are you the most intelligent person in the room but grumpy half the time?
10. On a scale of 1-10, how old are you?
11. Are you my appendix? Because you give me this weird tingly feeling and I kinda want to take you out.
12. Is it just the WiFi, or am I totally feeling a connection?
13. What’s one super power that you would never want to have?
14. Did you do anything interesting today, well besides talking to me?
15. If life is a video game, what cheat code would you want to use most?
16. What is the cheesiest pick-up line you’ve ever tried?
17. What was fun to do once, but you’ll never try to do again?
18. Is a hotdog a sandwich?
19. Are you missing me in your bed right now? YES or Yes? (This is also a good flirty, and funny goodnight question to ask a guy over text message)
20. What’s your all time favorite meme?

Related – The Best Cute, Fun, Flirtatious Text Messages To Send To A Guy

Funny But Also Random Fun Questions To Ask A Guy

Asking random questions is undoubtedly a great way to get an interesting and funny conversation started with a guy you like. Where it goes from there who knows? But one thing that you can count on for sure, is that you’ll both be having a great time along the way.

1. What movie do you quote most often?
2. What is a useless topic you know a lot about?
3. When you’re in a bad mood, who or what can cheer you up?
4. Did you ever buy something outrageous that you later regretted?
5. If you could only hear one song for the rest of your life, what would it be?
6. If your life had a theme song, what would it be?
7. You can only use one for the rest of your life: ketchup, ranch, or hot sauce. Which do you choose?
8. Which part of your body is the most ticklish?
9. What is the first law you would change if you were president?
10. What is the most surreal dream you’ve ever had?
11. What is the most sexiest and least sexy name?
12. What’s the weirdest thing you’ve every seen your pet do?
13. If you were an amateur wrestler what would your name be?
14. Would you rather only wear Crocs for the rest of your life or only watch Katherine Heigl movies for the next six months?
15. What’s the first thing you would do if a zombie apocalypse breaks out?
16. What’s the best prank you’ve ever played on someone?
17. Would you rather feel itchy all the time or ticklish?
18. If you could re-name your parents based on their personalities, what would their names be?

Funny And Interesting Questions To Ask A Guy

Delve beneath the surface and build a connection with him by asking him one of these cool and interesting questions. That are also fun and silly and hopefully leave him and you both laughing at his playful yet interesting answers.

1. How would you get yourself fired if you could?
2. Would you rather talk like a pirate at all times or have a parrot on your shoulder at all times?
3. What song would you play on repeat if you wanted to annoy someone?
4. Which type of clothing do you no longer want to wear but can’t get rid of?
5. What’s the dad best joke you know? 
6. If you could date any fictional character, who would it be?
7. If you were a DJ, what would your DJ name be?
8. What’s the most embarrassing haircut you’ve ever gotten?
9. If animals could talk, which do you think would be the rudest?
10. Which animal would be the flirtiest?
11. What chain restaurant would you refuse to eat at even if you were desperate?
12. What do you consider the worst condiment?

1. If you could be invisible for a day, where would you go and why?
2. What was the worst purchase you’ve ever made?
3. What’s the funniest name you can think of for a pet?
4. What is the funniest name you have actually heard used in the real world?
5. If you were a ghost, how would you haunt people?
6. What is the worst name you can think of to give your future child?
7. What would you choose as your animal sidekick if you were in a movie?
8. What’s the funniest thing you’ve ever seen a kid do?
9. What’s the most paranormal thing that has ever happened to you?
10. Did anyone ever convince you of something that you later found out was totally wrong?
11. What’s one thing that never fails to make you laugh?

Funny Online Dating Questions To Ask Him

Figuring out what to message a guy online can be nerve racking. Break the ice with one these funny online questions to ask a guy. These questions are good to ask on a traditional dating site like Match, or on a dating app like Bumble, Tinder or Hinge.

1. Does swiping through this dating app count as “exercise”?
2. How would you describe yourself in three emojis?
3. That dog looks so cute, can you give them my number?
4. Do you believe in love at first swipe, or should we unmatch and then match again?
5. If you could only have 3 Apps on your phone, what would they be?
6. How about I start this conversation, and you can start the next one?
7. My mom just asked me what “WAP” meant… any advice on how to navigate that conversation?
8. What’s the worst opening line you’ve even got on a dating app? And no it can’t be this one 😉
9. Going to Starbucks, need anything?
10. Serious question…is our anniversary when we first matched or when we first messaged?
11. Your bio had me on the floor. Wanna link up sometime and tell each other dad jokes?
12. If we were in high school, how would you ask me to prom?
13. What’s your go-to karaoke song?
14. Would you rather have hiccups for the rest of your life or constantly feel like you have to sneeze?

Related – How To Start A Flirty Conversation With A Guy Over Text (+ Example Questions)

Funny Yet Deep Questions To Ask A Guy

Getting to know a guy and develop a healthy relationship with him is a process that takes time. But who says it has to be boring! These personal questions are funny but deep at the same time. Enjoy!

1. What’s the first thing that ran through your mind when you first saw me?
2. If you had one day left to live, what would you do first?
3. What are some things that are okay to do occasionally but definitely not okay to do everyday
4. Are you good at keeping secrets?
5. Have you ever been to a psychic? What happened?
6. In your friend group, what are you most known for?
7. What’s the most unique characteristic you have?
8. What’s something everyone should experience at least once in their life?
9. If you had to flee the country, where would you choose to live?
10. When you are daydreaming, what do you dream about?
11. If you could anywhere in the universe for one day, where would you go?
12. What looks like it should taste better than it does?

1. What conspiracy theories make total sense?
2. Given the chance, what would you say to your five year old self?
3. What do you think you know a lot about but probably don’t?
4. What would be the most embarrassing thing to have a phobia of?
5. What is the funniest dream that you had that you can recall?
6. What is your favorite body part on yourself?
7. Has a sappy commercial ever made you cry?
8. What is the most embarrassing halloween costume you have ever worn?
9. What do you think is the most embarrassing thing to buy at a convenience store?
10. Serious question, pineapple on pizza yay or nay?
11. If you were a rapper, what would your rapper name be?
12. When you were a kid, what was your ultimate dream job?
13. Have you ever gone a day without wearing underwear?

How Do You Make Him Laugh?

To make a guy laugh, ask him funny questions, tell him jokes and be playful around him. Take notice of what he laughs at the most. As well as what kinds of jokes that he likes to make. Once you know what his sense of humour is you can ask him more funny questions and make more jokes about similar things. Overtime you will build a rapport with him and be able to make him laugh whenever you want. 

If you know that you want to make someone laugh with a fun question. Like a guy you’re interested, a crush or even your boyfriend, but aren’t sure how.

Now you can use this handy list of funny questions to ask a guy to make him laugh and to get a playful conversation going.

And if you need even more incentive or think that asking a fun or silly question is a bit awkward. Consider this, in one study by Jeffrey Hall from the University of Kansas, after analyzing a whopping 39 studies on the importance of humour in a relationship came to an interesting determination.

That yes indeed a couple who laughs together stays together. But it’s not just about the laughing. It’s about the shared humor that the couple has created together over time. Which helps to keep their relationship going.

Here’s to fun and funny conversations, laughing with an amazing guy and all the cool questions that ignite them!

**Your Next Step**

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**More Great Questions & Ways To Talk to Guys**

121 Clever Texts To Send To A Guy You Like (Flirty + Irresistible)

3 Best Questions To Ask Him On Your 1st Date (To Help You Tell If He’s The One)

200 Cute Goodnight Texts For Him (To Make Him Melt)

21 Conversation Starters And Ice Breaker Questions For A First Date

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