161 Weird Questions To Ask Your Boyfriend And Get Him Talking

Whether you’re bored of basic convos or just looking to shake things up, these weird questions to ask your boyfriend are perfect for adding some fun, unpredictability, and genuine connection to your chats. From really weird questions to ask your boyfriend over text to fun hypotheticals and crazy scenarios to ask your boyfriend in person, this is your ultimate list of playful prompts to nudge your man to open up. Be prepared to be surprised, amazed, and may be even a little shocked, as these questions peel back layers to his personality you hadn’t yet discovered. 

Why Ask Weird Questions In A Relationship?

Asking your partner weird questions might sound silly, but it’s actually a brilliant way to learn more about him and create meaningful memories, in the process. These fun weird questions to ask your boyfriend reveal his quirks, spark laughter, and bring you closer in the most unexpected ways.

In long-term relationships, it’s easy to fall into the same old conversations. But throwing in a few really weird questions to ask your boyfriend breaks that cycle. Whether it’s a late-night pillow talk session or you’re looking for weird questions to ask your boyfriend over text, these prompts add surprise and depth to your dynamic. That’s why we’ve curated this massive list of crazy scenarios to ask your boyfriend that range from flirty and random to downright hilarious.

• Helps break the routine and spark laughter
• Reveals hidden quirks and personality traits
• Encourages vulnerability in a lighthearted way

161 Weird Questions To Ask Your Boyfriend

Normal is overrated and light, playful moments don’t get the credit they deserve in bringing two people closer together. Give these weird questions to ask your boyfriend a try and find out for yourself.  Whether you’re newly dating or deep into a long-term relationship, these questions can instantly flip the script and infuse fresh energy into your dynamic. From fun weird questions to ask your boyfriend during a cozy night in, to totally unexpected weird things to talk about with your boyfriend while texting, these offbeat prompts open the door to meaningful laughs, wild imagination, and real bonding.

Related Reading: 5 Cute Ways To Improve And Strengthen Your Relationship

Weird but deep questions to ask your boyfriend

These weird questions to ask a boyfriend are perfect when you want to dive beneath the surface, but in a fun, unexpected way. They often lead to stories you’ve never heard and sides of him you’ve never seen.

1. If your personality were a flavor of chips, what would it be?
2. What’s the weirdest thing you secretly believe?
3. If aliens landed tomorrow and asked you to represent Earth, what would you say?
4. Would you rather be respected or remembered?
5. What’s something you’d never admit to anyone else, but might tell me?
6. If your younger self could see you now, what would he say?
7. What thought scares you but you think about it often?
8. Which emotion do you wish you felt more often?
9. If your life were a conspiracy theory, what would it be?
10. What would be the title of your autobiography if it had to be bizarre?
11. If you could see one hidden truth about yourself, what would you choose?
12. What belief do you have that no one agrees with?
13. If your inner child could talk, what would he tell you today?
14. What’s the most irrational fear you’ve never told anyone about?
15. Would you want to know how you die, if you could?
16. If your mind had a theme song, what would it be?
17. What’s your weirdest recurring daydream?
18. Do you think there’s a version of you in a parallel universe doing something crazy?
19. If you could erase one memory, but it meant losing all related feelings, would you do it?
20. What’s one weird thing that always makes you emotional?

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Strange ‘what if’ questions to ask your boyfriend

These are the best weird questions to ask your bf if you love throwing wild curveballs into your conversations. Strange, surprising, and downright creative, these “what if” questions and scenarios are perfect for shaking things up. 

21. What if you woke up in my body for a day?
22. What if dogs could talk but only to you?
23. What if you had to swap lives with a cartoon character for a year?
24. What if your mom and I switched bodies, whose advice would you trust?
25. What if you had to eat one weird food forever like jellyfish or tarantula?
26. What if you had a secret superpower but it only worked when you farted?
27. What if everyone suddenly forgot your name, how would you prove who you are?
28. What if you found out you were living in a simulation, would you try to escape?
29. What if your dreams were actually memories from another life?
30. What if you had to marry the last fictional character you watched?
31. What if you turned into a plant, what kind would you be?
32. What if you could only talk in animal sounds for a week?
33. What if I could read your mind once a day, when would you hide your thoughts?
34. What if mirrors actually showed alternate dimensions?
35. What if every kiss gave you a superpower?
36. What if people’s moods changed the color of their skin, what color would you be most?
37. What if we switched voices for a week?
38. What if you had to relive one random day from your past over and over again?
39. What if your pet could spill all your secrets?
40. What if your Google search history was tattooed on your body?

Related Reading: 125 Questions To Ask Your Boyfriend to Test His Love For You

Gross and hilarious questions to ask your man

Get ready to laugh and cringe. These weird things to ask your boyfriend are all about leaning into the gross, awkward, and unexpectedly hilarious moments that build emotional intimacy through humor.

41. Would you rather never brush your teeth again or never shower again?
42. What’s grosser: drinking expired milk or eating a raw onion?
43. If burps had flavors, which one would be the worst?
44. What’s the most disgusting thing you’ve ever smelled?
45. Would you eat a stranger’s toenail for $10,000?
46. Have you ever peed in the pool and lied about it?
47. If you had to name your poop like a pet, what would it be?
48. What’s grosser: boogers or belly button lint?
49. If I dared you to sniff your own sock after a workout, would you do it?
50. Would you rather always have sweaty hands or constantly itchy feet?
51. What’s a gross habit you’ve never told anyone about?
52. Would you lick the bottom of your shoe for ₹50,000?
53. If you could fart glitter, would you do it all the time?
54. Have you ever sneezed so hard that something weird happened?
55. What’s the worst bathroom emergency you’ve had in public?
56. What’s the weirdest thing you’ve ever picked out of your teeth?
57. If someone dared you to eat a spider, would you?
58. Have you ever worn the same underwear twice in a row?
59. If I cooked something terrible, would you eat it to be polite?
60. Would you rather kiss a pig or smell my socks after a workout?

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Weirdly flirty questions for your bf

These weird questions to ask your boyfriend are perfect for flirting with your man and pushing the boundaries of imagination to forge a deeper connection. Perfect for couples who like to keep things cheeky, fun, and a little unpredictable.

61. If I turned into a frog, would you still kiss me?
62. What’s the weirdest compliment you could give me right now?
63. Would you rather cuddle in a cave or a blanket fort?
64. If we were the only people on Earth, what weird date would we go on?
65. What odd thing do you find weirdly attractive about me?
66. Would you still love me if I spoke in cat noises?
67. Can you invent a secret language just for us?
68. If love had a smell, what would ours be?
69. What’s your ultimate awkward-yet-romantic fantasy?
70. Would you serenade me in public if I dared you to?
71. What animal do I most resemble when I sleep?
72. Would you still date me if I had a tail?
73. If I had a laugh like a goat, would you still think I’m cute?
74. What’s a weird nickname you’d give me that no one else can use?
75. If we had to wear matching outfits daily, what would they be?
76. If we wrote a cheesy rom-com, what would the title be?
77. Would you rather slow dance in the rain or eat ice cream in the shower together?
78. Would you wear a shirt that says “Property of My Girlfriend”?
79. What’s a weird flirty thing I do that you secretly love?
80. If you had to describe kissing me using only fruit, what would it be?

Related Reading: 69 Flirty Dares Over Text To Spice Things Up

Super random questions to puzzle your boyfriend

These weird things to talk about with your boyfriend have no rhyme or reason, they’re just plain ridiculous and fun. Great for when you want to keep the vibe spontaneous and silly.

81. If you had to name a planet after me, what would you call it?
82. What’s the weirdest world record you think you could beat?
83. If your shadow had a personality, what would it be like?
84. If you could swap noses with an animal, which one would you choose?
85. If cereal could talk, what would your favorite brand say to you?
86. Would you trust a fortune cookie that always came true?
87. What kitchen utensil matches your personality?
88. If your thoughts had sound effects, what would mine sound like?
89. What’s the weirdest item you’d take with you during a zombie apocalypse?
90. If you could rename a color, what would you call blue?
91. Do you think insects have a fashion sense?
92. If we lived in a treehouse forever, how would you decorate it?
93. If you could trade eyebrows with someone, who would it be?
94. Would you rather sleepwalk or sleep talk for the rest of your life?
95. What’s your conspiracy theory about squirrels?
96. If you had to wear one Halloween costume every day, which one?
97. If we were stuck in a musical, what would your solo be about?
98. Do clouds get jealous of balloons?
99. Would you eat a cake shaped like my face?
100. If your laugh were a musical instrument, what would it be?

Related Reading: 55 Serious Questions To Ask Your Boyfriend

Silly questions to ask your boyfriend over text

Need weird questions to ask your boyfriend over text that will make him laugh on the go? These quick, quirky prompts are great for mid-day fun or late-night giggles.

101. If your hands could talk, what would they say?
102. If you could shrink any object and carry it in your pocket, what would it be?
103. Can I be your human pillow forever?
104. What emoji best represents your current mood?
105. If I turned into a sandwich, what kind would I be?
106. Would you rather have spaghetti hair or pancake feet?
107. If our texts were turned into a novel, what would the title be?
108. What would your superhero name be if texting were your only power?
109. If your pet could text you, what would they say about me?
110. Would you rather only text using GIFs or voice notes?
111. What’s the weirdest voice message you’ve ever sent?
112. Should we start a secret texting language?
113. If autocorrect started roasting you, would you still use it?
114. Can you send me a duck emoji every time you miss me?
115. Would you rather have a phone that reads your mind or one that changes your voice randomly?
116. What’s a word you’ve typed wrong so many times it’s embarrassing?
117. If you had to end every message with a song lyric, which one would it be?
118. Do you ever talk to your phone when you’re alone?
119. If you had to choose one emoji to describe our relationship, what would it be?
120. Can we have a texting rule, where one day a week, we pretend to be aliens?

Related Reading: 51 Deep Relationship Questions To Ask For A Better Love Life

Bonus: Weird questions to ask your bf, Reddit edition

Inspired by real Reddit threads, these weird questions to ask boyfriend have been shared by girlfriends around the world. They’re equal parts hilarious and oddly romantic.

121. “Would you still love me if I had no bones?” 
122. “If I turned into a sock, which drawer would you put me in?”
123. “Do you think ants ever celebrate birthdays?” 
124. “Would you rather kiss me or have unlimited pizza forever?”
125. “If I had a clone, would you date both of us or just the original?” 
126. “If I were a worm, would you take me to Paris?” 
127. “Would you rather cuddle with me for 24 hours or have free Wi-Fi forever?”
128. “If I got turned into a hat, would you wear me?”
129. “Would you still date me if I spoke only in riddles?” 
130. “If I had spaghetti for hair, would you help me shampoo it?” 
131. “Would you still love me if I turned into a cardboard cutout?”
132. “If I disappeared and came back as a pigeon, would you recognize me?”
133. “Would you still date me if I were obsessed with frogs?”
134. “If I were a burrito, would you unwrap me or eat me whole?”
135. “Do you think our souls high-five in another dimension?”
136. “Would you still be with me if I grew a third eye that only cried glitter?”
137. “What would you do if I started narrating your life in an opera voice?”
138. “If I had a button that changed your haircut daily, would you let me press it?”
139. “Would you follow me into a haunted bakery?”
140. “Would you still date me if I barked at other girls?”
141. “If we could time travel to any date together, what weird event would you choose?”
142. “Would you be okay if our future child were born with wings?” 
143. “What if I turned into your favorite video game character—would you date me harder?”
144. “Would you eat cereal from my shoe if it were the only food left?”
145. “If I turned into a meme, would you share me or keep me to yourself?”
146. “If we had to spend a week as sock puppets, what would we do?” 
147. “Would you cry if I stopped sending you random selfies?”
148. “Do you think love exists between chairs when no one’s looking?” 
149. “Would you still propose to me if I were dressed as a clown?”
150. “If we could only speak in bird calls for a day, how would you say ‘I love you’?”
151. “Would you wear a T-shirt with my face on it to meet your boss?”
152. “Would you go on a reality show with me called ‘Weird Love’?”
153. “Would you dig through trash with me to find a sentimental receipt?”
154. “Would you still love me if I lived in a vending machine?”
155. “What would you do if I started sleeping in the bathtub ‘for balance’?”
156. “Would you carry a photo of my baby teeth in your wallet forever?”
157. “Would you fight a goose for me?”
158. “Would you let me tattoo my name on your forehead for April Fools’?”
159. “If we had to communicate through interpretive dance, how would you say ‘Let’s order food’?”
160. “Would you name a star after me or a sandwich?”
161. “Would you still date me if I had a tail and it wagged when I saw you?”

Final Thoughts

These weird things to ask your boyfriend aren’t random but a clever means of discovering and rediscovering each other in the most playful, personal ways. Whether you’re laughing at a bizarre ‘what if’ or melting over an oddly sweet compliment, these weird questions to ask your boyfriend help you connect on a level that’s genuine, silly, and heartfelt all at once.

You don’t always need candlelit dinners or deep, emotional talks to feel close. Sometimes, it’s enough to wonder aloud if he’d still date you as a burrito. Because when you can be weird together, you know it’s real. 

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