100 Weird [And Unusual] Questions To Ask A Guy

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There are a plethora of weird and unusual questions to ask a guy friend, whether he is your friend or your love interest. Guys usually like weird questions because they’re funny and bring out a whole new goofy side.

So if you’re looking for unusual weird questions for a guy you like… look no further than this 100 idea article!

Table of Contents

1. Do you have any food horror stories? What happened?

Has he gone out to a lovely place and gotten food poisoning? Or has he made the ultimate nasty meal for an important work or family dinner?

2. What is a game you play and always win?

Is he the competitive type with board games, card games, or sports games? Does he always win war or basketball?

asking a weird guy weird questions is fun

3. What is the most important thing on your laptop?

His photos, duh!

4. What is something weird your hometown is known for?

Do they do some weird marching parade, a big Thanksgiving event, or what?

5. Do you have any odd family traditions? Share.

Is he cute with and around his family? Does he have traditions that he will pass down to his own family?

Hey there! Wait up!

If you’re looking for questions for any other situations, be sure to check out these articles:

  1. Flirty questions to ask your boyfriend
  2. Funny first date questions
  3. Deep questions to ask a guy
  4. Sexual questions to ask your boyfriend

See, there’s no reason to be stuck on one type of question!

6. How do you perceive dating?

Does he think it’s shallow with Tinder or Bumble, or does he like that you can meet anyone anywhere?

7. Do you think dating has gotten better or worse over time?

Is he the old fashioned and sweet type of guy?

8. What is something you never have enough of?

Time. time. time.

9. What is your most embarrassing story?

Hopefully he get’s red in the face thinking about this one.

10. Is there anything you would tell everyone not to do?

What has he done that he regrets? Is there anything?

11. How many hours have you stayed awake in a row?

24 hours in a row of no sleep, or more?

12. What is the most beautiful wedding you can imagine?

Does he go for the classy church building, or the sandy sea with waves crashing?

13. What is the most spectacular funeral you can imagine?

Or instead, a celebration of life.

14. Do you consider yourself an airhead?

Or is he dense?

15. Are you in touch with reality or do you create your own?

Maybe he does both. Ahh, a man of many worlds.

16. What is the most useful thing your parents taught you?

How to love?

weird girls like asking guys weird and unusual quesions

17. What did you do as a kid that kids no longer do today?

Go outside… but for real, kids are glued to their phones and iPads these days.

18. Do you think technology has enhanced quality of life?

Maybe some of his, but probably not.

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19. If you could replace a body part what would it be?

If he says his dick please run.

20. What movie do you wish your life was more like?

Probably an action movie with lots of cool cars and hot girls.

21. Have you ever broken your phone?

Like thrown it across the room in anger? I guess this would be the perfect weird question to ask over text!

22. What is your favorite thing about being male?

Once again… if he says his dick, run.

23. What is your least favorite thing about being male?

He’s probably going to bring up something regarding privilege.

24. What is something people assume about you that is wrong?

Assumptions… are they ever right?

25. What is the most fascinating piece of trivia you know?

Fun facts, let’s hear them.

26. Which celebrity would make the worst leader?

Here comes Donald Trump.

27. What is something you are tired of?

These questions…

28. What is a double standard that needs to end?

Maybe he will be enlightened and say something about women’s rights!

29. What is your greatest achievement this far in life?

Is he proud of himself?

30. Who is your favorite author?

What kind of books is he into?

31. Which Harry Potter house do you belong in?

Is he a Gryffindor or a Slytherin?

32. When was the last time you cried?

Is he soft? Emotions make him strong.

33. When was the last time you laughed so hard you cried?

The Joker?

34. What is the sickest you have ever been?

Has he contracted COVID?

35. Have you ever had a one-night stand?

One and done? Or a relationship kind of man?

36. What is your biggest kink?

If he says he doesn’t have any, he is lying.

37. What is the biggest lie you ever told?

Did anyone find out? How was it handled?

38. What is something you are ashamed of?

About himself, not about someone else.

39. Is there any type of girl you would not sleep with?

Or is he an all-encompassing type?

40. Has anyone ever attacked you for your beliefs?

What are his beliefs? Is he Muslim, Buddhist, Christian, Agnostic?

41. What is something you find very touching?

Touching hands, touching you, touching me!

42. If you had to marry an actress now who would it be?

One that looks just like you!

43. If you had all the money in the world what would you do with it?

Spend it on you hopefully.

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44. What is the most boring thing in the world to you?

Monotony, repetitiveness?

45. If you could have any job what would it be?

What would he choose to do if money wasn’t a priority?

46. Do you have a foot fetish?

The numbers for those are high… way too high.

47. Do you like legs or butts more?

Where do his eyes wander?

48. Do you prefer tan skin or pale skin?

Sun kissed or protected?

49. Blonde hair or brown?

Beauty waves or mountain straight?

50. Would you rather have fame or money?

Or fame that makes you money?

51. Have you ever cheated on anyone?

If he has he isn’t a good person. Sorry. No exceptions.

52. What is your biggest phobia?

Spiders? Heights?

53. What is your sun sign?

Is he an emotional Cancer, a detached Virgo or a crazy Gemini?

54. What is your rising and moon sign?

He will probably look at you like you are speaking a foreign language.

55. Do you even believe in astrology?

The houses, the charts, all of it!

56. Do you believe in God?

Our Father who art in heaven!

57. How often do you go out vs. stay in?

What’s his idea of fun?

58. Do you like cartoons?

Does he watch them often? Which ones? Anime?

59. Do you consider yourself liberal or conservative?

Or libertarian? Probably an extremist or neither if he’s in this generation. It seems to be all or nothing.

60. If you put out a magazine what would you name it?

Something naughty or nice?

61. Blue or green?

Or a combination of the two like seafood green?

62. Do you think women are more intelligent than men, in general?

Of course he does… that’s why men have larger egos.

63. Do you like trampolines?

Bounce. Bounce. Bounce.

64. If you were in the witness protection program what would you call yourself?

Does he have some crazy name he wants to be called?

65. Have you ever been banned from a public place?

What was it for? Public nudity?

66. What do you want to have written on your tombstone?

Words are all we have.

67. What is your favorite transportation mode?

Plane, train, car, boat?

68. What is the funniest adventure you have been on?

Let’s see if he can recreate it and make you laugh too!

69. What conspiracy theories of you believe?

Does he want to make one up of his own?

70. If you could trade places with someone who would it be?

Does he want to Parent Trap the world with someone?

71. Do you like kids?

How does he feel around kids?

72. Do you want any when you’re older?

Does he want any of his own?

73. Do you believe in right and wrong?

Or are morals made up by humans who have power to keep power?

74. What are the morals and standards you live by?

Does he believe in living with integrity? In living without causing others or himself pain?

75. Have you ever fallen for an older woman? Like a teacher?

Does he fantasize about moms?

76. Who is your number one role model?

Does he live like the motto “what would God do?”

77. Who is your hero?

We could be heroes just for one day.

78. What is your favorite kind of music?

Is he a pop fan or a country man?

79. Do you enjoy concerts and festivals?

How’s he feel about getting groovy with strangers?

80. Would you consider yourself creepy?

Like if he looked at how he lives his life… is he a creep?

81. How would your ex describe you?

Ex’s usually have a pretty good idea. Would she say you’re shallow?

82. What seems delicious but tastes terrible?

Lot’s of cakes.

83. If you could join the Olympics which sport would you partake in?

Skiing, snowboarding?

84. What would be the silliest thing to fill a piñata with?

Whatever the opposite of candy is, so veggies?

85. What is your favorite joke?

Is he the classic knock knock type?

86. What is the coolest thing you have done by yourself?


87. How do you show love?

Is he a hugger? Or does he write poems and songs for those he loves?

88. How do you need to be loved?

Is it the same way he shows his love?

89. What is your first thought when you wake up?

To pray? To sing? To get rid of the morning breath?

90. Do you pray or meditate?

Or meditate on what to pray about?

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91. Do you think clothes show a lot about a personality?

Or are clothes simply clothes?

92. How do you feel about age?

Does age bring limitations on abilities?

93. Do you like experimenting with new things?

Sexually and non-sexually…

94. Do you enjoy traveling? Or are you a homebody?

Crab or wanderer?

95. Would you rather be single or in a relationship?

Depends on the girl most likely.

96. Pringles or goldfish?

Random. They are both oh so yummy.

97. Who is the third person on your missed call list?

See who likes to talk to him on the phone. Probably his momma!

98. Who is someone you would enjoy punching in the face?

An ex-best friend? A teacher? A parent?

99. How many times a day do you look in the mirror?

Is he just confident or is he cocky?

100. Have you ever had a crush on your best friends girlfriend?

That’s a little taboo but haven’t we all?


These are some odd questions that will surely get you some weird answers. But weird is good and good is fun.

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About the author 

Coach Colt here, the founder of Dating Armory, your go-to source for no-nonsense, practical relationship advice. I'm a bisexual male in a same-sex open relationship and a researcher in sex, love, and relationships with 7+ years of experience. I specialize in helping both men and women navigate the crazy world of dating.

Don't miss my other guides packed with practical dating advice (no bullshit repeated Platitudes) and tons of real life examples:

My Top 57 First Date Ideas That Always Work (As a Dating Coach)

Are Coffee Dates Good? It (Kinda) Depends

17 Basic Coffee Date Tips (From a Dating Coach)

How to Get a Gay Boyfriend: 25 Tips That Work