Skip to Content

165 Funny Questions To Ask A Guy To Make Him Laugh

165 Funny Questions To Ask A Guy To Make Him Laugh

Men like to be entertained. They’re looking for a woman who is laid back, isn’t always stressed and angry, and knows how to have a good time. So, if you’re trying to secure that second date, then you’ll definitely need some funny questions to ask a guy to make him laugh!

These questions will definitely make you appear like you’re an all-around fun, outgoing, and open-minded person.

Everyone tries to present themselves in the best possible light in the beginning, and there’s nothing wrong with that. After all, you’re contemplating starting a relationship with this man, so you don’t want him to think you’re just another average girl.

By making him laugh with these unique and fun questions, you’ll help him see the best side of you.

It’s scientifically proven that couples who laugh a lot tend to have a more satisfying and fulfilling relationship. So getting a man to laugh now could build a great foundation for a healthy and laughter-filled relationship in the future.

Making a good first impression is crucial when you’re trying to make a guy pursue you. Unfortunately, you’re being judged every second. Your potential partner is wondering whether or not he’s really into you and if he actually wants to see you again.

On the other hand, you’re nervous as hell, which makes it all too easy to be extremely serious. Trust me, that’s not really the first impression you want to give a man.

However, if you can make light of the situation and find a cool way to break the ice, that will definitely bring you closer to your goal. And before you know it, he’ll start to chase you.

Funny questions to ask a guy to make him laugh (awesome ice-breakers)

DONE! 165 Funny Questions To Ask A Guy To Make Him Laugh

These questions are great when you’re trying to get the conversation going. Men, just like women, won’t respond to boring or uncreative questions. That’s why you have to think outside of the box when it comes to getting a guy to like you.

1. What was your first job ever? What did you like/dislike about it?

2. If your life was a show, what would the theme song be?

3. If the last thing you ate is the only thing you can eat for the rest of your life, how soon will you die?

4. What’s the worst haircut you ever had?

5. Have you ever been drunk on the job?

6. What was your favorite Halloween costume you wore as a child?

7. What’s the funniest animal you owned as a pet and what was its name?

8. What are your favorite songs from your childhood years that you still listen to when nobody else is around?

9. What’s the most embarrassing moment from your teenage years?

10. What is the weirdest thing you’ve ever eaten for breakfast that’s not breakfast food?

11. Which words did you have difficulties pronouncing as a kid, so you made up your own?

12. If you had the chance to live on Mars, but could never come back, would you do it?

13. What did you get into the most trouble for with your parents as a kid?

14. What’s the funniest event that ever happened on a family vacation trip? Did you ever get lost with your parents?

15. What’s the most ridiculous thing your parents ever did to embarrass you?

16. What show on Netflix have you binge-watched embarrassingly fast?

17. What’s your real favorite book, and what book do you pretend is your favorite to sound smart?

18. Which Disney character does your life most resemble and why?

19. What is the most stressful situation you’ve ever been in your life?

20. What’s the worst mistake you ever made as a kid and how did you manage to get away with it?

DONE! 165 Funny Questions To Ask A Guy To Make Him Laugh

21. What silly animal are you inexplicably afraid of?

22. Have you ever lied about a talent to impress someone?

23. What was the first concert you ever went to?

24. How many siblings do you have and who was the bully growing up? Are you the black or white sheep of your family?

25. What song do you totally like that everyone else thinks is basic or annoying?

26. Have you ever ripped your pants in public and how did you hide it?

27. Has anybody ever walked in on you while you were busy in the bedroom?

28. Name any movie that you found was boring, but you kept on watching because of the person sitting next to you?

29. What would you do if you ran out of toilet paper in a public bathroom?

30. Have you ever been attacked by a wild animal? If not, what would you do if you were?

31. Do you have any of those weird hobbies when walking down the street, like counting your steps or stepping on even tiles?

32. With your Instagram pictures, which filter do you use the most?

33. If you were told that you can do anything without suffering the consequences, what would you do?

34. What was your reaction when someone caught you singing even though you thought no one was listening?

35. Can you think of a word that makes you laugh uncontrollably?

36. What was the worst prank that you played on one of your friends?

37. Have you had an embarrassing moment that you now consider to be funny?

38. What’s the worst slip of the tongue you’ve experienced?

39. What is the worst joke you ever heard yet laughed at deliberately?

40. Have you ever accidentally broken something and then hidden the evidence?

Funny questions to ask a guy to make him laugh: School & work edition

DONE! 165 Funny Questions To Ask A Guy To Make Him Laugh

Sometimes you just want to get to know a person better and be funny at the same time. If that’s your goal, then you can try some of the following questions.

1. Who was the worst teacher you ever had, who was the best, and why?

2. What afterschool activity did you do as a kid?

3. What part of elementary school or kindergarten do you wish you could apply to your adult life? For example, naptime?

4. Were you ever caught texting during class by your teacher?

5. Has it ever happened to you that you accidentally called your teacher Mom or Dad?

6. Did you ever have a crush on one of your teachers? Who was it?

7. Did your crushes ever find out that you liked them if you didn’t tell them directly?

8. Did you and your friends ever decide to skip class to do something fun and interesting?

9. Did you ever make a huge mess during art classes?

10. Did you ever lie about one of your skills so that your crush would notice you?

11. Were there any awful school performances you were forced to join?

12. Did you ever go to school hungover?

13. What was your worst detention in school?

14. Were you ever caught cheating during a school test?

15. How many people did you date in high school?

16. What was the worst nickname that you and your coworkers have given to your boss?

17. Would you be courageous enough to get drunk with your boss?

18. What is the absolute worst or grossest job you would do for a million dollars?

19. What was the weirdest noise you heard during a meeting then pretended like nothing was wrong?

20. Were you ever caught doing something against the rules in the office? How did you react?

21. Did you ever think you were texting someone else something funny, but then you accidentally sent it to your boss?

22. Have you ever thought about what it would be like to date your boss?

23. What’s the weirdest thing you’ve ever seen happen at a company party or team-building event?

24. What would your coworkers put on your dating profile about you?

25. What is the most boring part of your work that you always enjoy doing?

Funny relationship questions to ask a guy to make him laugh

DONE! 165 Funny Questions To Ask A Guy To Make Him Laugh

Are you looking for tips and tricks to make your relationship stronger? Well, sometimes it only takes a joke or two to strengthen your bond. Not only will you have more fun together, but you’ll also learn more about your significant partner in the process.

1. If our relationship was a movie, what do you think the title would be? Which actor would play you? And which actress would play my part?

2. There are many great romantic movies out there, but which one do you think best describes our love story and why?

3. Are there any weird or gross things you’re still shy to do in front of me? Is there anything I can do to make it easier for you?

4. What is your weirdest habit you’re still keeping hidden from me?

5. What part of a kids’ movie completely scares you?

6. What was the worst nickname someone has ever given you as a child?

7. What do you think is my most embarrassing habit and why?

8. Do you have any unusual or cheesy date ideas that you’ve been dying to try out?

9. Did you ever think you were texting me, but then you accidentally sent the message to someone else?

10. What funny song would you pick for our wedding ceremony?

11. What do you think is the funniest thing that you did for me?

12. What went through your head when you first did something silly in front of me?

13. If you were stranded on a desert island with one actress, who would it be?

14. If you ever found a magic lamp, would you mention me in your wishes?

15. What is the goofiest compliment you ever received from another woman?

16. Which superhero do you think I resemble the most?

17. If you had to compare me with an animal, which one would it be?

18. On a scale of lame to extremely cheesy, how romantic do you think you are? What would you say are your weakest areas?

19. If you could give me a different name based on my personality, what would my name be and why?

20. What’s the worst thing you’ve done to me but never had the courage to spill?

Funny questions to ask a guy you like to make him laugh

DONE! 165 Funny Questions To Ask A Guy To Make Him Laugh

Being on a date with a guy you’re into can be nerve-racking. In situations likes these, there’s a high chance that you may not be able to express your feelings. You may run out of words because of nervousness.

But these questions can help you in that time of crisis:

1. If someone asked you to draw a portrait of you, how would you like it to be?

2. If you could get a chance to be an actor, would you take a role of a serial killer, superhero, or something else?

3. What are the best and worst lessons you have learned from your previous relationships?

4. If you had one chocolate left and you were surrounded by the people you love the most, who will you give it up for?

5. Were you afraid of ghosts or aliens as a child?

6. As a kid, who was your biggest role model?

7. What’s a particular secret only you and your grandmother/grandfather know about?

8. What movie do you have no desire to watch before dying?

9. Which song would play in your head while in a fight with someone?

10. Would you jump out of an airplane on your honeymoon?

11. If you could design your perfect dream house, how would it look?

12. If scientists could increase the lifespan of humans by 100 years, what do you think would be the consequences of such action?

13. What’s the worst present you ever received in your life?

14. What’s one song that you could always listen to no matter the circumstance?

15. Do you enjoy riding bikes with your significant other or are you more of a solo rider?

16. What’s your favorite science fiction movie and why?

17. Have you ever lied in your past relationships?

18. How would you react if a woman proposed to you in public?

19. Do you believe that love at first sight can lead to a healthy marriage?

20. What is your idea of a perfect Valentine’s Day?

21. What Disney/cartoon character were you inexplicably afraid of as a kid?

22. What’s a funny (appropriate) pick-up line that works for you?

23. What website are you embarrassed to admit you visit on a regular basis?

24. What’s your weirdest talent?

25. If you were in jail for something terrible, what do you think would be your crime?

26. What’s the most embarrassing dance move you’re secretly awesome at?

27. What was the strangest punishment your parents ever gave you?

28. If you were stuck on a desert island with your significant other, which food would you bring with you?

29. Have you ever put on makeup just for fun? If yes, do you have any pictures as proof?

30. If you had to put one fruit on a pizza, which one would you choose and why?

Funny questions to text a guy to make him laugh

DONE! 165 Funny Questions To Ask A Guy To Make Him Laugh

Tap into your sense of humor to help you score a couple of points while getting to know a guy over text. Once he sees your questions are playful and lighthearted, he won’t be able to resist you and will definitely ask you on a date with him.

1. What was the weirdest cartoon you watched growing up?

2. If you had the ability to be invisible, what would you do and where would you go first?

3. Who is the person you despise the most and would never want to bump into?

4. Which movie makes you cry every time?

5. What is the most appealing animal on earth?

6. What do you believe is your worst purchase to this day and why do you regret it?

7. Do you believe you could live for a month without any money?

8. If you could dye your hair any color, which one would you choose and why?

9. What are your favorite songs to sing in the shower and while driving?

10. Would you rather swim in shark-infested waters or run through a field surrounded by lions?

11. If your pet could speak, what do you think would be their opinion of you?

12. If you had to erase one day of the week, which one would you eliminate and why?

13. What was the most ironic thing that you participated in or witnessed in person?

14. Do you believe that animals talk with each other behind our backs?

15. What was the creepiest toy you owned as a child?

16. What quote is always stuck in your mind?

17. What is the strangest thing you have ever seen on the internet?

18. If you were to come back as a ghost, who would you haunt first and why?

19. If you could, which part of your body would you replace?

20. How would you react if you happened to see your doppelganger walking down the street?

21. If you were a color, what would you be?

22. What is the strangest thing you’ve done while you were at home alone?

23. Do you think you could live in a woman’s body for a week?

24. What commercial jingle gets stuck in your head all the time?

25. If your life were a newspaper article, what would be the headline?

Funny hypothetical questions to ask a guy to make him laugh

DONE! 165 Funny Questions To Ask A Guy To Make Him Laugh

It’s always fun to throw in a couple of hypothetical questions – there’s no right or wrong answer. And bonus, the following questions will encourage him to open up to you.

1. If your best friend had the opportunity to pick a tattoo for you to get, what would they choose?

2. If you could choose one famous person to be your best friend, which celebrity would you pick?

3. If you had tons of money, what totally unnecessary thing would you splurge on?

4. If you wrote a book about your life, how many pages would it contain?

5. If you had the ability to switch places with anyone in your family for a month, who would it be?

6. If you were the president, what would you change about your country?

7. If you could be an Olympic athlete, what sport would you want to excel in?

8. If you could only eat at one restaurant forever, what restaurant would it be?

9. If you were trying for a talent show, what act would you perform?

10. If you could only listen to one song for the rest of your life, which one would you pick?

11. If you had to sell your soul to the devil, what would be the terms of the deal?

12. If you could go back in time to witness one historical event, which one would it be and why?

13. What invention do you think should be erased from history?

14. If you were invited on the first passenger trip to the moon, would you go?

15. What one material possession would you save if your house was on fire?

16. Would you live life differently if nobody could ever judge your actions?

17. What skill would you pick if you knew you could master it in 24 hours?

18. If you were to release your own fragrance, what would it smell like and what would you call it?

19. If you found a friendly alien in your house, what would you do – would you call the cops?

20. Would you rather have the opportunity to see the Loch Ness Monster or Bigfoot?

21. If you were a secret agent, what would be your code name?

22. If an underwater city existed, would you be scared to visit it?

23. If you were a hippopotamus, how would you lose weight?

24. If you had to fight Muhammad Ali, who do you think would win?

25. Would you still date me if I was a worm?

165 Funny Questions To Ask A Guy To Make Him Laugh