100 Random Questions to Ask a Guy in 2023

Check out these different and random questions to ask a guy to help get the conversation flowing!

In this post:

• Funny Questions To Ask a Guy
• Get To Know You Questions To Ask a Guy
• Conversation Starting Questions To Ask a Guy
• Personal Questions To Ask a Guy
• Juicy Questions To Ask a Guy

Funny Questions To Ask A Guy

1. What is the funniest joke you have heard?

This is a simple question but could tell you a lot. This question allows you to get a sense of humor.

Plus, you may get a good laugh out of it, and you can share a funny joke as well.

2. If you had to pick one, would you want to best friends with the Easter Bunny or Santa Claus?

I mean, haven’t we all thought about this from time to time? It is definitely a random question and one that will make him think.

It will probably catch him off guard, but it could definitely make for a good conversation starter, depending on his reasoning

3. What is your most embarrassing moment?

We have all had an embarrassing moment at least once in our lives. You are lying if you say you haven’t.

So why not get some laughs in by swapping stories and bonding over your times of embarrassment.

4. What meal would you not want your last meal on Earth to be?

This is the opposite kind of question you are expected to be asked. Everyone gets asked what you would want your last meal to be.

You’re never asked what you would not want it to be. This one will definitely get the conversation started.

5. What do you think the funniest movie is?

Everyone has a movie that they think is hilarious. So why not talk about it?

He can share his and talk about why he thinks it is the funniest, and then you can share yours. You may disagree, but at least the conversation is flowing.

6. What is the grossest food combination you can think of?

Get to know what his taste buds are like. Does he think the same foods are gross that you do? This will also show how creative he is.

7. What word do you think is the funniest or sounds made up?

This may reveal some information about him you may not have known about. Maybe he will choose a word you were not expecting or have never heard of.

8. If you could make up a word, what would that word be, and what would it mean?

This gives him another chance to show off his creative side. Does he go for something boring and not too creative?

Or does he come up with something extremely unique that catches you off guard?

9. What two body parts would you want to switch?

This is definitely a conversation starter. If he picks something that does not make sense, have a discussion about it, or share what two body parts you would switch.

10. If you woke up as a cat, what would you do?

This can show off his imaginative side. What does he think a cat does? Also, does he answer quickly, or does he take a while to answer?

11. If you could wake up in the body of any animal, what animal would it be?

This may reveal a lot about him. What animal does he identify with? Or does he pick his favorite animal?

12. What is the one thing that you would say to end any conversation?

See what direction he takes to answer the question. Does he go the funny and weird route? Does he go for shock value to catch people off guard?

13. If you couldn’t shower with water, what would you replace water with?

This one will get a funny answer for sure. This is definitely not something that I have thought about.

He most likely hasn’t given it any thought either, so it will be funny to see what he chooses.

14. How do you think fruits got their names?

Have you ever thought about this question? I have not, but it would make for an interesting conversation.

See what stories he creates. You can each take turns coming up with stories for different fruits.

15. What ridiculous law would you create?

This question offers another chance to show off some creativity. See how ridiculous he goes. The sky’s the limit. Does he go simple?

Or does he go extremely creative and come up with something off the wall?

16. What is the weirdest dream you have had?

This could bring some interesting and funny stories. He may have had some weird dreams that will make you laugh. You can share yours as well, if you choose.

17. What is the worst superpower?

Everyone always asks what the best superpower is, or what their superpower would be.

This changes it up and asks for the worst superpower. Maybe the one he thinks is the worst is the one you think is the best.

18. Would you rather be too hot or too cold?

I have a strong opinion on this question. He may have a strong opinion on this as well.

19. What’s worse — bed head or hat hair?

Both situations are bad hair situations. There is no right or wrong answer, but it will be interesting to see which one he picks.

20. What is your go-to karaoke song?

This one can say a lot about a person. It can reveal what music he likes, and what music he likes to sing.

If he refuses to answer and says he doesn’t sing karaoke, then it reveals he is no fun.

“Get to Know You” Questions To Ask a Guy

21. What is your zodiac sign?

For many people, this reveals a lot about a person. It can make or break a relationship. So if you are into zodiac signs, make sure to ask this question.

22. Are you a dog or cat person?

Everyone is one or the other, and they usually have a strong opinion on why.

23. What is your dream job?

Get to know what career goals he has. Is he working toward his dream job? Or is his dream job completely opposite of what he is doing now?

24. If you were granted three wishes, what would you wish for?

This is a classic question that can reveal a lot. Does he wish for wishes? Does he wish for money? Or does he help others?

25. If you had one day left to live, what would you do?

I think we have all thought about what we would do before the end of our lives. If he hasn’t, this is his time to think about it.

26. Who is your favorite musical artist?

As someone whose life revolves around music, this is a very important question. What type of music someone listens to can say a lot about a person.

If they do not listen to much music, or don’t have any favorite artists, that also says a lot.

27. What is your favorite food?

Get to know what type of food he enjoys. Maybe you two have similar tastes, or maybe you’ll be introduced to a new type of food.

28. What is your secret talent?

Many people have talents that no one expects. Even if it’s something small, talent is a talent.

29. If you could be any character from a movie or TV show, who would you be?

Maybe he identifies with a specific character. Or maybe, he just really likes and wants to be one of the characters from his favorite TV show or movie.

30. What’s your favorite color and why?

This is a simple question, but it’s always a good question to ask. It’s a good way to start a conversation and to get to know someone.

31. If you could travel anywhere, where would you go?

I love traveling and want to see the world, so this is a very important question. It shows his curiosity about the world around him.

32. What is your favorite outdoor activity?

If you are an outdoorsy person, this will be an important question to ask. Is he an outdoorsy person to begin with? Or does he prefer the indoors?

33. What is your favorite board game?

I love a good board game, and I have a few that I enjoy the most. Plus, this will help brainstorm some future date ideas for the two of you.

34. What is your favorite place you have visited?

Everyone has a place they loved when they visited.

This will definitely help you get to know some stuff about his past, and you can share yours as well if you would like to.

35. What is your favorite type of cheese?

Who doesn’t love cheese? I mean, of course, if he is lactose intolerant, maybe not. But cheese is still delicious.

36. What is the biggest puzzle you have solved?

Solving a puzzle needs dedication. The larger the puzzle, the more time it takes. So this could show how dedicated he is as a person.

37. What is your favorite movie genre?

I think everyone has a favorite movie genre. If it is your least favorite genre, that can lead to a conversation.

38. What is the worst injury you have ever gotten?

Everyone gets hurt from time to time. Perhaps, he is more clumsy and has some funny injury stories to share.

39. What is one item you cannot live without? It can’t be your phone.

I feel like your phone is the go-to answer for everyone. Force him to think outside the box with this question. Plus, it shows what he cherishes in his life.

40. What is one topic you could talk about for hours?

I have several topics that I am passionate about and could talk about endlessly.

If he has anything he is passionate about, he should also have something he could talk about for hours.

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Conversation Starters-Questions To Ask a Guy

41. What is your favorite kitchen appliance?

Doesn’t everyone have a favorite kitchen appliance? It could be the most useful, or just one he likes the best.

42. What is your favorite zoo animal?

Not just any animal, what is his favorite zoo animal. This will also reveal his thoughts on zoos.

43. What is a movie you think is better than the book?

This can be a very controversial question. Some have very strong opinions on this topic, so this can definitely lead to a discussion.

44. Do you prefer watching movies or reading books?

Many people have one they prefer over the other. So if you each have a different preference, you can debate which one is better.

45. Is mashed potatoes Irish guacamole?

This one goes back to a debate that divided my roommates, and I and sparked a week-long survey. So this can definitely be a conversation starter.

46. Is a hot dog a sandwich?

This is a never-ending debate that many have a strong stance on. So why not open the debate and bring this question to the table.

47. Is there a difference between cakes and cupcakes?

For some, they are different; for others, they are the same. He might have no opinion on the topic, or he might have never thought about it before.

48. Which is superior — ice cream cake, cookie cake, or regular cake?

This is a very important question. Each one is delicious, but one is superior in everyone’s minds. Which one he prefers could spark a debate.

49. If you had to lose one of your five senses, which one would you lose and why?

It is hard to imagine losing any of your senses, and a case can be made for losing each one.

So it would be interesting to hear which one he chooses and what his reasoning is.

50. If you had to move to one state you have never been to for the next five years, which one would you choose and why?

Five years is a long time to be stuck in one place, so you have to choose carefully. This involves much thought and could definitely lead to an interesting conversation.

51. If you could get any tattoo with no consequences, what would you get and why?

Let’s be honest, everyone has a tattoo they want to get that is a bit questionable. So why not discuss what tattoos you would get without any backlash or criticism.

52. Does movie theater popcorn really deserve the hype that it receives?

Now, I love movie theater popcorn. But for some people, it may not be as good as everyone thinks.

53. Would you rather see a movie at home, in a theater, or at a drive-in?

The way you watch a movie may affect how you like the movie. Some may even have a strong preference, and others maybe have never experienced a drive-in movie.

54. If you could create a flavor of a Dum-Dum lollipop, what would you create?

This one will once again show off his creativity. What kind of fun sucker flavor can he think of? Will it be boring? Or completely out of left field?

55. What was your favorite PBS Kids TV show growing up?

Many of us watched PBS Kids shows growing up and had a favorite one.

If he didn’t watch PBS Kids, he was missing out, and you can teach him about all the wonderful shows.

56. Have you ever been in a fist fight? If so, what was the best one? If not, what is the closest you have been to getting in a fight?

This one will bring up some stories for sure. If he has never been in a fight or close to one, then this one is boring.

But almost everyone has at least gotten close to a fist fight.

57. Which grocery store is the best and why?

This one reveals so much about a person’s personality. Does he prefer small or large grocery stores? Local or a chain? Busy or slow?

58. What movie scared you for life as a child?

Did you watch a movie when you were younger that left you having nightmares for days?

Maybe you watched it when you were too young. Maybe it’s a surprising answer.

59. Do you have any irrational phobias?

Sometimes, an experience growing up can cause some irrational phobias. This one can help you learn more about his past and get some interesting stories.

60. Disney, Nickelodeon, or Cartoon Network and why?

Everyone has a preference. Which one he chooses better have some good reasoning behind it, and there will be a discussion to follow.

You may see one as superior, and he may see a different one as superior.

Related: 55 Romantic Questions To Ask Your Boyfriend

Personal Questions To Ask a Guy

61. Who was your role model growing up, and who is it now?

Who did he look up to as a child and did that change as he grew up? You can also talk about why that person was a role model.

62. What is a pastime or hobby someone would not guess about you?

This may reveal some surprising things about him. Talk about how he discovered that hobby and why he enjoys it.

63. What was your dream job when you were a child?

What ridiculous job did he want to have? Did he want to be a superhero? Does it relate to what he does now?

64. What was your most impactful work moment?

This could be an embarrassing moment, an awkward moment, or something that changed his perspective on things. Have him share the story and how it impacted him.

65. What is your best or favorite memory?

Everyone has a memory that stands out in their mind.

This question will provide a look into his past. It will show the moments he cherishes and the ones that helped shape him.

66. What is a memory that always makes you laugh?

What memory does he look back on and just cannot help but laugh hysterically? It may be funny to just him, but either way, it has a story.

67. What is the most pain you have inflicted on yourself?

Everyone has their clumsy moments from time to time. What was a time when he injured himself maybe a bit more than other times?

68. What is the closest you have come to death?

Has he ever had a near-death experience? If he has, there is definitely a story to be shared.

69. What are some names you have thought of for future children and/or pets?

I know I have a list of names that I like, and this is the time to see if he does as well. What names does he like and why? If he doesn’t have a list, help him make a list.

70. How many bones have you broken?

Has he broken a bone? How many and how did he do so? If not, has he come close to breaking a bone?

71. Have you ever binge-watched a show, and if so, which one?

This is not just watching an entire show from start to finish. This means sitting down and watching a show for hours non-stop. We have all done it, so now is the time to fess up.

72. If you were on the show My Strange Addiction, what would you be on it for?

What is the weird habit or quirk that may be worthy of a TV show episode?

This could be a make-or-break moment. How weird is the answer, and does he have an explanation?

73. What pets have you had, and what pets do you want in the future?

Is he an animal person? Has he had a bad or good experience with pets?

74. What’s the worst drug you have taken?

He may have never taken any drugs before. He may also have some fascinating stories to share, or he may not share anything. You won’t know unless you ask.

75. What are you a hoarder of?

Does he have way too many shirts? Does he have a collection of some sort that other people may say is too much?

Maybe he doesn’t hold on to anything and just has what he needs.

76. If you had to get an impromptu piercing, what would you pierce?

What would he pierce if he had to? Would he go for something he could hide, or something obvious? Why did he pick that place?

77. What do you consider the dumbest decision you have ever made?

He must have something that he’s done and looked back on and cringed.

It may be something small, but we all have that decision that we think back on and know it wasn’t the smartest decision.

78. What is the best compliment you have ever received in public?

What compliment did a stranger give him that stood out to him? Why did it stand out? This can lead to a great conversation.

79. What is the number one thing on your bucket list?

What is the one thing he wants to do before he dies? Is it something he has a plan for? Is it something you can help him achieve?

80. Weirdest thing you got caught doing when you thought no one was watching?

Was he singing and dancing in the kitchen when he didn’t think anyone was home? How weird and embarrassing was it, and how did he get caught?

Related: 100 Flirty And Dirty Questions To Ask A Guy You Like

Juicy Questions To Ask a Guy

81. Boxers, briefs, or nothing?

Everyone has a preference. What is his preference and why?

82. Are you a virgin? If not, how old were you?

This is definitely a conversation starter. Open the conversation with this, or you can just slide it into the conversation later on.

83. Number of partners?

This is another great conversation starter. This one will definitely bring up some stories and other interesting topics of conversation.

84. Fruit or vegetable smoothies?

This is a literal juicy question. Does he prefer juice and drinks from fruits or vegetables? Everyone has a preference.

85. Who is your celebrity crush?

If he says he doesn’t have one, he is lying. Everyone has a celebrity that they find attractive in some form. Now is the time to spill who he likes.

86. Did you ever have a crush on a high school teacher?

Did he have a teacher that caught his attention? Why did that teacher catch his attention? What subject did they teach?

87. What is your alcohol of choice?

Time to pick his poison. What alcohol does he enjoy the most, and was there a time he enjoyed a bit too much of it?

88. What is your favorite boy band?

As someone who grew up loving One Direction, the boyband someone prefers says a lot.

For some, there may only be one correct answer, so he should answer carefully.

89. What would be your drag or stripper name?

Some people have given this much thought and already have it planned.

Does he go for a play on words? Or does he go for something similar to his actual name?

90.Do you prefer a back, neck, or leg massage?

What is his favorite place to receive a massage? Does he prefer to give or receive massages?

91. Are you a member of the mile-high club?

If the answer is yes, time to share the story. If the answer is no, what are his thoughts on it?

92. Did you ever get sent to the principal’s office?

Was he a troublemaker in school? Share your memories and stories of time in school growing up. Maybe he was someone who avoided trouble and followed all the rules.

93. Most awkward break-up story?

Sometimes breakups can be messy. Maybe he had one that did not go well, or maybe there was one that caught him off guard.

He may have had only nice and amicable break-ups. If so, he is lucky.

94. Weirdest encounter on a dating app?

If you two met on a dating app, this is even better. Maybe he ran into someone he knew and it was awkward. Maybe he had a weird conversation. Maybe he had someone become obsessed with him.

95. What is the oldest you would date?

Does he have an age cut-off? Maybe he will date anyone no matter how old they are. Regardless of his answer, a conversation will for sure follow.

96. What is your guilty pleasure?

He can answer the question however he wants. This question can be answered in many different ways. It all depends on interpretation.

97. What is your craziest sexual fantasy?

Does he want to share this with you?

This could work as a conversation starter or something to end your conversation with. It will definitely help continue the conversation.

98. What is your best pick-up line?

He may have used it in your past conversations already. Or maybe he was saving it.

99. Have you ever peed in public?

Everyone has encountered a situation where they really had to go. Maybe it resulted in having to use the great outdoors.

100. If you could be described as an animal, what animal would you want to be described as?

Once again, a question that could be taken in many directions.

See how he chooses to answer. He may already have an answer and reasoning ready to go.

That is a wrap on the guide of best random questions to ask a guy. Small talk and getting to know someone can be awkward and difficult.

Hopefully, these questions will help get the conversation going with the new guy you are talking to.

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