Funny Questions to Ask A Guy

Funny Questions to Ask A Guy

This article is going to give you not only a list of funny questions to ask any man to get him talking, cultivate a connection and make him want to spend more time with you… this article will change your entire view on humor and how it relates to men and your relationship success.

So please read until the end because first I want to get to the questions and explain some rules to guide you and then get into the heart of what will make or break your interactions and give you insight on how you can use humor to get men talking like you would not believe.

So first, understand that humor is one of the most important things in human nature, and especially in relationships. Who wants to sit around calmly talking in world of monotony? We need laughter to spice up our lives, and more importantly relieve a little stress.

Beyond that… more importantly… humor is a way to a man’s heart.

I don’t know how to be any clearer. If you laugh with him he will want to spend more time around you. This is pretty much true for all men. Don’t worry—I will explain this later on and make it all crystal clear for you.

I have found laughter to easily be at the heart of every great relationship. Laughing with the one you love is not only an amazing feeling, it is also extremely unifying. It connects you and makes you feel like you have a “shared experience” with the person.

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…

How to Be Hilarious

But how can you be funny, you might ask? The idea of “being funny’ might seem impossible but the truth his… it’s scarily simple. I have created a list of funny questions for you to ask a guy that will make him start sharing. As he shares, he will view you as someone pleasant he enjoys being around. The act of sharing will be what creates a bond, you do not have to come up with anything—all you have to do is participate and enjoy.

Warning: everyone has a different sense of humor, so don’t jump the gun and delve into questions without knowing the person. The one danger with certain humor, is it can be offensive- humor is subjective- and the last thing you want to do to anyone is to offend them on a moral and personal level.

MORE: 50 Great Questions To Ask A Guy

Here is the list of funny questions to ask a guy: (the most universal and safe to ask)

  1. If you had to marry any actor who would it be and why?
  2. What would be the most insane thing you would buy or do if you won the lottery?
  3. Have you ever been caught in an “embarrassing” situation?
  4. What’s the most cringe-worthy thing you’ve ever experienced?
  5. What is the worst thing that ever happened to you in high school?
  6. Strangest lie you have ever told?
  7. What’s the craziest thing you would do? And how much would you have to get paid to do it?
  8. What’s the dumbest celebrity name you’ve ever heard?
  9. Do you have any odd or eccentric family members?
  10. If you had one outfit you had to wear for life what would it be?
  11. If you were cast-away with one person on a desert island who would it be?
  12. Who is the last person you would choose, and why?
  13. If you were arrested what would be your closest friends’ first suspicion?
  14. What in your mind would be the worst job ever, and why?
  15. What’s the most awkward thing a girl or guy has ever done to you?
  16. Have you ever been jealous of anyone?
  17. If you could be animal what would you be, and how do you reflect this animal?
  18. What’s the dumbest is take you ever made?
  19. Have you ever been caught “red handed”
  20. What time period would you choose to live in if time machines existed?
  21. What’s the funniest thing you have ever seen?
  22. Have you ever been pranked?
  23. Have you ever pranked anyone?
  24. 24. Were you mischievous as a teenager?
  25. What’s the most trouble you’ve ever been in with your mom?
  26. What the last thing you’d want your family to know about you?
  27. What’s the grossest thing you have ever done?
  28. Grossest thing you’ve ever seen?
  29. Grossest thing you have ever done?
  30. If you were invisible what would you do?
  31. If you were the opposite for a day what would be the first thing you would do?
  32. Who is your biggest fantasy lay?
  33. Who would you rather die than hook up with?
  34. If you could beat up anyone in the world who would it be?
  35. What is the most annoying thing that has ever happened to you?
  36. If you wanted to be the most annoying person in the world what would you do?
  37. What’s your favorite comedy?
  38. Have you ever fake cried?
  39. What is the funniest joke you’ve ever heard?
  40. If you had one thing to change about you what would it be?
  41. If you had to dress as any stereotype what would be your last choice?
  42. Have you ever broken something on purpose?
  43. What’s the stupidest decision you’ve ever made?
  44. If you ever owned a yacht what would be your most ridiculous name for it?
  45. If you had to marry one person, have sex with another, and then kill the last who would those three people be?
  46. What’s your least favorite hairstyle?
  47. What’s your worst sexual experience?
  48. If you could eliminate one music genre what would it be?
  49. If you could make anything legal what it be?
  50. If you were invisible what would you try to get away with?
  51. What would be the most ridiculous way to settle a disagreement if you had a choice?
  52. If you could make anything free what it be?
  53. What is your funniest inebriated experience or party experience?
  54. Would you rather live in a nudist colony or be celibate for life?
  55. If you had the ability to be invisible what would you do?
  56. What is the weirdest thing you find funny that most people would not find funny?
  57. If you could get away with murder who would you kill?
  58. Have you ever been in a ridiculous accident?
  59. What’s the most dangerous thing you’ve ever done?
  60. What’s the dumbest fashion statement you’ve seen?
  61. What’s the dumbest trend to you?
  62. What is your favorite outfit on a woman?
  63. What is the craziest fashion trend that women love but you hate?
  64. What would be the best way to quit your job?
  65. Weirdest dream you’ve had?
  66. If you could go back in time, what fictional character would you be?
  67. Do you think time travel would be fun?
  68. Is your life a series of crazy events or have you had a pretty plain existence?
  69. What is your weirdest memory from childhood?
  70. Do you ever play pranks on friends? If so, weirdest prank?
  71. Have you ever done something stupid you are embarrassed about?

There you go.

Use the questions and watch the guy you are interested in react. His reactions will give you a clear idea of what he truly finds funny. His sense of humor will give you a roadmap to what makes him feel good. If a man laughs and feels good around you, that will carry over to other areas of your relationship.

Different Strokes

Just remember everyone has a their own sense of humor. Everyone will find a certain thing funny that someone will not. The most important thing is to always remain comfortable, and do not try. Just be you… which is to say: Be the way that you are when you’re with the people you’re most comfortable with. Be comfortable.

The more honest you are with your humor the more real the connection will be just have fun and don’t take someone who doesn’t find your sense of humor funny as any sort of insult.

It’s not you or them—it’s just not a match made in comedic heaven. Always look for what connects with you and never try to force a relationship, or most importantly from this article- a joke!

MORE: How To Never Run Out of Things To Say On a Date

If I meet a girl who shares my sense of humor (which I will admit is not mainstream by any means) some may say “politically incorrect”- I will instantly have an attraction and connection. Laughter is one of the best gauges of how someone truly feels, or what they truly think.

Ask yourself… what do you find funny? Do you have a unique sense of humor that would surprise people? This will be a good thing to know about yourself first so that when you come across a guy who shares this unique sense of humor you are able to identify it and align with it. Don’t focus on trying to adapt to a man’s sense of humor; focus on understanding your own and only concern yourself with men who also align with that.

Humor Can Reveal Hidden Parts Of Who We Are

My mom wears conservative designer clothes and pearls and looks like a saint, won’t swear, is by all means the image of a mature refined woman, goes to church, but will literally cry and shriek with laughter at some of the raunchiest jokes and comedians. I know my mom, so I can see through her facade, and the image she wants to portray to society, but to an outsider they would be shocked at what she’s laughing at. My point here is that people unintentionally reveal themselves through laughter. What someone laughs at is as important as what they say if not more.

Men Love Funny Women

Men love funny women, this is pretty much across the board—but the idea of being funny might seem difficult. Well, it’s not. The reason it seems difficult is because you have to feel truly uninhibited and comfortable while being humorous. But when you try to be funny you come off as if you are trying to impress. Trying to impress is an automatic way to not end up “impressing.” Try to think of it as… both of you either align well or not—so your sense of humor will align with his or it won’t—no one is “wrong” or “bad.” Your sense of humor simply aligns or it doesn’t.

Never “Fake It”

I’m sure you have faked a laugh at some point in your life. I have as well. Trust me there’s nothing worse than pretending to think something is funny then having to belt out a fake laugh. Its uncomfortable and not going to make anyone happy.

It won’t make you happy, either! Why pretend when you could be spending time with someone you truly do enjoy laughing with? Why laugh when it’s not funny? It’s actually pointless to laugh when you don’t find something funny—for your own sake! Don’t waste your own time!

Also if your acting unnatural how can you have an honest connection through humor you don’t really find funny? It would be impossible. You might feel that faking it in the short term is a good idea to make him like you… but if you do this, you will not be able to sustain this façade you create. Even more, you will not give off the vibe that makes someone funny!

MORE: Ask A Guy You Like These 20 Cute, Amazing Questions

Humor Can Make A Man Open His Heart To You

Humor can really unlock a man’s heart.

I have a story about my own personal life that illustrates why you should never try to “fake” your sense of humor… I admit my sense of humor is kind of “out there” and many women would be horribly offended by it.

I am going to tell you a story that happened with a woman I was seeing that was the turning point for how I ultimately came to understand relationships. Even though this happened long ago, the awareness is still the same and I can say matters as much as ever.

So don’t be offended by what I am going to explain… I am going to give you a lesson about men that applies almost always that will change how you view relationships—and therefore change your relationship success.

Specifically, I am going to reveal exactly how to create a connection like nothing you have ever experienced before by being able to let a man expose his true thoughts, fears and hidden secrets he would never share. Yes, this is thar important.

I’m simply trying to illustrate a point for your benefit, to show you how humor can cultivate a true connection like nothing else can.

I was watching a Bill Burr stand up with a woman… He goes on to make a joke about hitting women, saying “how can you say that there’s no reason to hit a woman? I mean you shouldn’t do it… the people who do should be buried beneath the prison, but to have the audacity to say every beating just falls out of the sky is insane. Do women just walk on water? I don’t get it!?”

The crowd was silent, I was silent. He then says, ” why is it so quiet right now?!!” I thought, ” damn he went for it.” My girlfriend at the time starts laughing hysterically, and then goes on a rant about how annoying girls can be by pretending to be innocent little flowers, and how she literally avoids girls, and has always gravitated towards male friends.

I was taken aback and realized if she thinks that’s funny, I could go further and say anything I want without being concerned about offending her. I realize this was a turning point in how I viewed relationships in general.

Being able to say what I wanted made me have no filter; this lack of a filter create a bond deeper than any bond I had with any woman—things I once thought were “outrageous” became acceptable and even normal to say!

I would never think in a million years this girl would even remotely laugh at this joke, being that wife beating is just about as popular a joke topic as cancer, or aids. The fact she liked Bill Burr, most importantly, and I did too was really cool, and got me to be more of myself, and move forward to a deeper connection.

Obviously all these subjects are about tragic subjects that aren’t funny, but I am bringing them up as examples here to illustrate the extremes. By seeing how wide the range of subjects I could joke about with this girl, it showed me that I had a lot of freedom within the relationship to express myself. And for a guy, freedom is one of the things we love the most in a relationship!

MORE: 110 Questions to Ask your Boyfriend

Humor Can Create A Bond Deeper Than You Know

I know it might seem odd, but not many girls I’ve met find the comedians I like remotely funny, let alone socially acceptable. I assumed she’d hate my affinity for crass humor so when she laughed at probably one of the most controversial jokes from one of my favorite comedians made my brain just go, “ding ding ding.”

What matters is not my own personal sense of humor but the lesson you can take away from it. When a woman can appreciate a man’s sense of humor—it will surprise and delight most men.

Most men assume that the woman they are with is going to judge or dismiss what they find funny—so let yourself listen and be “present” in the conversation and be comfortable with his sense of humor.

Funny Questions to Ask A Guy: Tips & Tricks

  • Don’t pretend to be comfortable if you are not.
  • Don’t interrupt when he is telling a story, let him tell it and see how “far” he will go (this gives you insight into who he really is)
  • Don’t say things to “seem” like you have the same sense of humor.
  • Don’t judge what he finds funny but don’t go along with something that offends you because you think he will like you better

This illustrates the heart of what makes a relationship succeed or fail—compatibility.

If your sense of humor is compatible, you have found a great match—or at least an indication that you have found a match.

When you can laugh with someone, you can work with someone and be on the same team. Being a partner means being able to be together and understand each other—so faking it makes you lose out on the chance of finding someone you jive so well with.

So to go back to my example, some women would have turned off the tv and complained after hearing the offensive comment. I took a risk putting him on but I also took a risk that got me a major reward—I wouldn’t just throw on an offensive comedy skit with someone I’m just meeting or trying to get to know, obviously, but when the time is right and you are getting to know someone… it’s going to be rewarding and significant for the future success of your relationship if you get to the core of who someone is.

Let humor be your guiding light into the darkness of the unexplored territory of his heart.

Trust me, this will change how he sees you and make him share his heart with you.

And the list of questions I gave you will invigorate the conversation, and get you to really find out the true internal thoughts in his mind. Yes, the things he hides from the world. Yes, the things you want to know that he would never tell you.

Just always remember, be natural. Have fun with the conversation. Please don’t try to impress, or try to be funny. Just be yourself, and always remain comfortable with what you’re saying.

Every relationship is different. Every man is different as well except when it comes to one thing. In every situation you have with a man, there comes a time where he says “yes” or “no” to you; it’s an internal process where he realizes he likes you or not, wants to be with you or not, takes you seriously and wants a serious future with you or not. Whether he says “yes” and gives you everything you want or “no” and shuts down, pulls away and could take or leave you… all boils down to this one thing. Do you know what that “one thing” is? If not, honestly, I recommend you read this or risk losing him forever: The #1 Thing Men Desire In A Woman…

funny questions to ask

Even more great questions to ask him:

125+ Crazy Dares for Truth Or Dare

425+ Never Have I Ever Questions: The Ultimate List

150+ Funny Questions to Ask a Guy or Girl

104 Interesting and Funny Questions to Ask a Guy

Want to find out if he really likes you? Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…

Take The Quiz: Does He Like You?

In summary:

  • Don’t ask questions you’re not comfortable with
  • Ask follow up questions
  • Be present
  • Humor is key to a man’s heart
  • These questions will work but don’t be shy about adding your own
33 comments… add one
  • naomi January 4, 2022, 10:49 am

    how would i know that my crush really loves inspite we did meet on our first meet up with him .He isn’t that talkactive actually he is a shy boy
    what kind of signs should i expect from him…

  • joyce June 12, 2018, 9:59 am

    I really like this questions bcoz make me to know alot of thing about his funniest

  • krista April 4, 2018, 2:51 pm

    just like women, men also are attracted to funny women. my boyfriend told me that he immediately fell for me when we started hanging out and talking about anything esp when we would just laugh. those are good memories!

  • emily April 3, 2018, 1:41 pm

    whenever i see my guy laugh, it makes me feel comfortable especially when i am feeling nervous. thanks to this article because i will always have hilarious questions to ask him.

  • karen April 2, 2018, 2:04 pm

    i believe that laughter makes the relationship stronger. my boyfriend and i didn’t have the most fun times when we started because we didn’t know how to. but when we started sharing our lives, even those most embarrassing memories, we started to really click and since then we realized we should be open and just have fun and laugh things off!

  • cindy March 28, 2018, 3:49 pm

    it is really a great experience discovering more about your guy but sometimes it is very difficult to think of what questions to ask him especially the funny ones. this post is worth reading! I learned more and i am excited to share it with my friends.

  • cindy March 28, 2018, 3:42 pm

    it is really a great experience discovering more about your guy but sometimes it is very difficult to think of what questions to ask him especially the funny ones. this article is worth reading. will share it with my friends.

  • samantha March 27, 2018, 7:59 pm

    these funny questions are really the best ideas. just don’t go too far and make a mess by sounding like you’re trying to be someone else. a guy would want a fun conversation but make sure you’re natural and having fun too.

  • latifah March 26, 2018, 3:51 pm

    i really learned a lot about how to start a conversation with my man at the same time being funny after reading this article. now, i know what are the safe and right type of funny questions to ask him.

  • poppy March 23, 2018, 12:24 pm

    Never ever fake humor! Sure, men like funny women. But trying too hard could ruin everything if it doesn’t feel natural.

  • mikaela March 22, 2018, 4:02 pm

    if you don’t know how to communicate well with your guy, then your relationship can be boring. i will take note of these questions to ask my boyfriend tonight and i am sure that it will be fun!

  • brianna March 21, 2018, 9:09 pm

    these are just the cutest! i love the questions you shared here, i can definitely use them to ask my man and it will sure be hilarious! haha, i can’t wait! =)

  • crissa March 20, 2018, 3:47 pm

    one thing i learned about guys is they will open up to you if you make them
    laugh. these funny questions are great! they will absolutely give me a gateway
    to my crush’s mind.

  • amelie March 19, 2018, 8:04 pm

    try to get to know the person before asking questions that can be sensitive based on his personality and beliefs. trying to be funny is really risky but once you get the hang of it, it’s so easy to get along with anyone even a crush.

  • natalia March 16, 2018, 4:32 pm

    i agree that humor is a way to a man’s heart. if a guy meets someone who he can laugh with, it means his future relationship is going to be fun and filled happiness.

  • farrah March 15, 2018, 9:38 pm

    for someone like me who isn’t funny at all..trying to be hilarious would be a challenge. but after reading all these ideas, i think i might be able to pull some of them. i’ll give this a try and hope that it will work for me and my man. :)

  • vanie March 14, 2018, 3:49 pm

    sometimes, it can be really hard to think of funny questions you can ask your guy. i am very fortunate to have come across this article! these questions will surely get some laughs!

  • ruth March 13, 2018, 2:59 pm

    if you want your man to talk and open up, these questions are the best way to go. being funny can make a lot of difference. your man will not feel like you’re interrogating or asking too may personal questions. this way, he’ll be more comfortable and you’ll both have fun.

  • nathalia March 12, 2018, 4:43 pm

    i am a firm believer that one way of getting to know your boyfriend better is by asking questions. and if you put a little bit of humor then your guy will become comfortable with you. i will take note of this funny questions and will prepare too for my boyfriend might ask me funny questions as well!

  • marla March 9, 2018, 3:30 pm

    men loves quirky, funny women and these ideas are the best ideas to ask away so you can both have a relaxed and fun conversation. i like these, thanks for sharing!

  • vina March 8, 2018, 7:07 pm

    i can’t help but smile right now. i just can’t imagine the weirdness for me trying to be funny. but i think these are worth the try. (=

  • selena March 7, 2018, 3:11 pm

    these ideas are so awesome, i’m laughing just thinking about how i’d talk about them with my! thanks for sharing these, i love them so much!

  • draya March 6, 2018, 1:52 pm

    i think these funny questions will work best for my boyfriend. i also love how some of the questions might give me some insight about his likes and dislikes. an example is a question What is the craziest fashion trend that women love but you hate?

  • marian March 5, 2018, 3:50 pm

    i am not really into asking people funny questions, even my boyfriend. but if that would change how he sees me and guarantee him sharing his heart with me, then i think i’m gonna start asking him the list of questions i have read in this article.

  • francheska March 2, 2018, 3:38 pm

    i noticed that as much as women love men with humor, men also like funny women. i guess along the way, you can weigh things and how much you can ask your men because again, men are all different.

  • mariah March 1, 2018, 11:30 am

    lol, these are just too funny and i can’t wait to use them with my crush! (=
    i hope i could really spend time with him so we can chat and get to know each other.

  • alexia February 28, 2018, 3:36 pm

    these are really funny questions! i bet my boyfriend and i will both be laughing by the end of every answer.

  • cheryl February 27, 2018, 3:47 pm

    i am interested in this one cute guy and i don’t know how to start conversing with him. i am happy i came across this article and found funny and safe questions i could ask him.

  • teresa February 26, 2018, 6:51 pm

    Asking funny questions are really great to start a conversation. If you’re too shy to ask him personal questions in the beginning, try these hilarious tips and you’ll both surely end up laughing really hard.

  • alexa February 22, 2018, 8:05 pm

    it’s true that men love funny women, but don’t try too hard that you seem as though you’re someone not to be taken seriously.

  • anneli February 21, 2018, 11:41 am

    these are surely fun ways to talk to your guy. be natural though and don’t try to hard it would feel fake.

  • maya February 20, 2018, 11:10 pm

    talking about these stuff would be really fun when you’re trying to get to know each other. i like the ideas you’re sharing!

  • francia February 19, 2018, 12:17 pm

    this is really funny stuff! i’ll keep a note on these ideas to ask my boyfriend, it’ll be so much fun!!

Leave a Comment