Since everyone enjoys a good laugh and a nice chat, I’ve compiled a list of amusing questions to ask your guy friends. 

Of course, everyone’s sense of humour is different, but I’m confident you’ll be able to come up with a topic that everyone enjoys debating and riffing on. 

Remember, these are only the beginning. It’s up to you to take the question and run with it to the locations you think the most amusing.

Questions to ask your guy friends for fun

1. Have you ever sucked your toe?

Make it clear that you didn’t mean to ask about their childhood days. It is blissful to know a secret of them…hehe. 

Followup questions

1. Why did you do it?
2. What was your age when you did it?
3. How did your toe taste? 
4. What else have you sucked?

2. What is the weirdest thing one of your bosses has ever done?

I’m sure we’ve all had that one boss who had a few screws loose or the teacher who had a nervous breakdown in class.

Followup questions

1. Have you ever lied to your boss? Why?
2. Is your boss a weird person or do you see him like that?
3. Are you okay with your boss?
4. Do you feel like quitting your job? why?

3. What’s the worst smelling place you’ve ever visited?

This one I tell you is really fun to ask because the responses you get are top-notch; you can not resist your laughter at any cost.

Follow up questions

1. Why did you go there?
2. What was the reason for that smell?
3. Why is it the worst?
4. Would you like to visit that place again?

4. What are some examples of your praises that are actually insults?

You might already know the answer to this but it is okay to make the person say it. Also, this can unveil some of their favourite slang too.

Follow up questions

1. How much do you use it?
2. What is your favourite slang?
3. What is your favourite cuss word?
4. Have you ever insulted me?

5. Which celebrity do you think deserves to date you?

See how your ideal type compares to that of a friend, whether you’re a guy or a lady. But if you’re as bad as me when it comes to celebrity names then pick any web series character or book character.

Follow up questions

1. Why do you think so?
2. Do you crush on that celebrity?
3. Who would you like to date?
4. Would you marry a celeb if they proposed you?

Wasn’t enough? Here are some more:

1. Can you show off your flirting skills?
2. Is your first love still enticing you?
3. Is there a question that irritates you?
4. When you want to hit on someone, what’s your go-to pick-up line?
5. Cute or sexy, which type of person do you prefer?
6. What one clear clue do you provide when you’re interested in someone?
7. Is your girlfriend/boyfriend envious of you?
8. Would you mind if I flirted with you a little?
9. Is there anything I can do to entice you to like me?
10. Tell a love storey on a modest gesture or personal detail.
11. What is the first thing you notice about someone on a date?
12. What would you do if you were in the position of having to seduce me right now?
13. What are your favourite forms of massages?
14. Do you have a tendency to become enraged quickly?
15. Where is the most romantic spot for a kiss?
16. What are some of the strangest places you’ve urinated or pooped?
17. What’s the most hilarious inside joke you’ve ever heard?
18. In a single sentence, how would you describe the internet?
19. How many chickens would it take to kill an elephant?
20. Would you want to sleep with your clone if you weren’t straight?
21. Would you have a great sex life if you could marry yourself?
22. What would you do if you only had 24 hours to live?
23. Who is your all-time favourite celebrity who is disliked by the general public?
24. Do you believe in conspiracies of any kind?
25. What do you think I’m thinking right now?
26. What do you think the most heinous manner to die is?
27. What exactly causes you to cry?
28. Do you have a fear of what other people think of you?
29. Which superpower do you think you’d never want to have?
30. What is the most embarrassing outfit you’ve ever donned?
31. What is the most inventive insult you can come up with?
32. Which part of your body would you like to be able to detach, and why?
33. What was formerly thought to be trashy is now considered extremely classy?
34. What’s the most inventive Wi-Fi name you’ve seen?
35. What is the most ridiculous fact you are aware of?
36. What is the most nasty quote you’ve ever heard from a real person?
37. Which historical person takes home the prize for being the most ruthless?
38. What is something that most people find simple but that you find difficult?
39. What basic adjustment in your life might you make that would have the most positive impact?
40. Have you ever arrived at a location dressed completely inappropriately?
41. If you could reincarnate as either a human or an amoeba, which would you choose?
42. Would you rather be named a tomato or a potato if you had to choose?
43. Have you ever written a love letter to someone?
44. When you’re about to meet someone you like, do you become nervous?
45. Will you watch a romantic or a scary movie on your date?
46. Would you like it if someone told you right now that they have a crush on you?
47. Are there any talents you’re not aware of?
48. Do you consider yourself to be a wise and amusing soul?
49. What are your thoughts on vast crowds of nude people?
50. What was the strangest proposal you’ve ever gotten?

The bottom line:

These are questions that can be asked of anyone, male or female. Although the questions are fairly general, I thought they would be entertaining to respond to like a man. You can also use any of the questions from our other fun questions page to ask a female.