With a handful of interesting questions to ask a guy, you can make the next hangout with the fellas anything but routine.

If you’ve ever felt stuck in a conversational rut, you know how a few well-placed interesting questions can shake things up. The hard part is coming up with questions to ask that will direct the conversation the way you want it to go.

In this post you’ll find tons of interesting questions to ask a guy on all kinds of topics, and with all kinds of uses… allowing you to have interesting talks with old friends and new bros in any situation.


5 Best Interesting Questions To Ask A Guy

Everyone knows the struggle of sitting next to someone and not having the first idea of what to talk about. Put the awkward silences behind you with one of these interesting questions.

The questions on this list cover a wide range of topics and work great in a pinch, so no matter if you’re with guys from work or reuniting with old friends, these questions are sure to get people talking.

Here are the 5 best interesting questions to ask him:

1. Any advice for your previous boss?

There must be a reason it's his previous boss, right?

2. What do you work toward in your free time?

Free time can be a chance to improve ourselves.

3. Which pet was most important to you?

Some bonds with pets can be incredibly strong.

4. If you had to give a TED talk tomorrow, what would it be about?

Find out what interesting things he's an expert at.

5. What fictional character do you identify with the most?

Is he a hero? A villain? A best friend?

4 Interesting Conversation Topics To Ask A Guy

Great conversationalists know how to get people talking about topics that matter. They know how to cut past small talk and find something meaningful to discuss.

Thankfully, anyone can develop that skill using these interesting conversation topics.

These conversation topics were chosen because they are universal. They open the door to topics that men care about and think about. Base your conversations on these big topics and you'll find conversations much easier to start and maintain.

Here are 4 interesting conversation topics to ask a guy:

6. Family

Regardless of how we feel about them, we all have one.

7. Relationships

Our relationships define us and they're a great conversation topic.

8. Politics

With mutual respect this tricky topic can be very meaningful.

9. Hopes and dreams

We spend so much time daydreaming, why not talk about it?

5 Interesting Conversation Starter Questions To Ask A Guy

Even a group of guys can have an awkward period before settling on something to talk about. Conversation starters are a foolproof way to break that tension and get people talking.

These interesting questions to ask your guys will help you fill the awkward silence with thought provoking conversations.

Here are 5 interesting conversation starter questions to ask a guy:

10. What’s your favorite ’90s jam?

Who doesn't love a conversation about the best throwback music?

11. What is the first thing you'd do if you heard about the outbreak of zombie apocalypse?

If he doesn't already have a plan... it's time to make one.

12. Which fictional villain is your favorite?

Good villains can be as memorable as heroes.

13. Would you rather have the super power of strength or invisibility?

Both have advantages worth comparing.

14. What do you think the absolute coolest hobby out there is?

This will let you talk about interests and passions.

4 Interesting Questions To Ask A Guy To Get to Know Him

This list is full of questions to ask a guy to get to know him on a more personal level. These questions will help you decide if the guy you’re talking to has what it takes to be a close friend or if he’s more acquaintance material.

These get to know you questions focus on men’s priorities, values, and beliefs… helping you get close without making you sound like an interrogator.

Here are 4 interesting questions to ask a guy to get to know him:

15. What are you known for?

And is he proud of that reputation?

16. Who do you idolize the most?

Who does he model himself after?

17. If you could learn to do anything, what would it be?

What new skill does he desire?

18. What is something you learned in the last week?

Life long learners make great friends.

5 Interesting Personal Questions To Ask A Guy

At the mention of personal questions, people generally start to put their guard up. That’s because we often relate personal questions to ask a guy with embarrassing secrets…

But the kind of personal questions we’re focused on are just interesting questions to ask him that focus on who he is as an individual.

These questions aren’t meant to pry out secrets, but to help you develop friendships through personal connections.

Here are 5 interesting personal questions to ask a guy:

19. What were you like in high school?

It's fascinating to look back on how we've changed.

20. What was the last experience that made you a stronger person?

Sharing these stories can be very encouraging.

21. What small thing makes you angrier than it should?

We all have pet peeves. What are his?

22. Would you rather correct a mistake from the past, or receive a message from the future?

Regrets or hopes, which is he more concerned with?

23. What rules do you make for yourself?

Every man needs a code.

4 Interesting Questions To Ask A Guy That You Can Also Ask Girls

You’re a busy guy, so we thought it might make things a little easier if we threw in some interesting questions to ask a girl on this list, too.

These questions have the playfulness you want in questions to ask a girl, but aren’t going to come across as flirty if you ask them of a guy you’re hanging out with.

Here are 4 interesting questions to ask a guy that you can also ask girls:

24. If you could pick only three songs to play over and over again, which songs would you pick?

Think of it as a soundtrack for life.

25. What is your biggest turnoff?

What would disqualify a potential date?

26. What have you really wanted to do for a long time but haven’t done yet?

There's no time like the present!

27. What event in your life would make a good movie?

Life is full of dramatic moments.

4 Interesting, Random Questions To Ask A Guy

Random questions to ask a guy can jump start a conversation just when it seems like you may be running out of things to talk about.

They’re a great way to transition from one topic to the next and spontaneity to your interactions. In short, random questions make conversations less uncomfortable and more enjoyable.

Here are 4 interesting, random questions to ask a guy:

28. Teach me something I don’t know in the next five minutes.

You'll be amazed at you can learn so quickly.

29. When scrolling through Facebook, Twitter and Instagram, do you prefer posts from celebrities that you have never actually met or from your best friends?

What does he see as the purpose of social media?

30. If you could be a member of any TV-sitcom family, which would it be?

He'd get all their drama, but all the laughs too.

31. What is in your fridge right now?

The contents of a man's fridge are a reflection of himself.

5 Interesting Funny Questions To Ask A Guy

Laughter has many health benefits... not to mention a good belly laugh is good for the soul.

That’s why it’s a great idea to have a few funny questions to ask next time you’re hanging out with your boys. Get the whole crew laughing along with a few questions from this list.

Here are 5 interesting funny questions to ask a guy:

32. What do you think about clowns?

Or does he try not to?

33. What’s the funniest lyric you’ve ever misheard?

And how did he realize he was singing it wrong?

34. Which is more believable: the Easter bunny or the tooth fairy?

Debating mystical creatures is always fun.

35. What is your lamest skill?

When you mastered, even odd tasks can be impressive.

36. What’s the most boring super hero you can come up with?

It'll probably get a movie deal anyway.

6 Interesting, but deep Questions To Ask A Guy

How often do you hang out with friends and feel like you never talked about anything meaningful? Catching up with the guys is great, but we long for deep conversations to draw people together and discuss life’s big issues.

Knowing deep questions to ask when the conditions are right can bring about the meaningful conversations we crave from time to time.

Here are 6 interesting but deep questions to ask a guy:

37. At what age did you become an adult?

What was his entrance into manhood?

38. The best part of waking up is?

What gives his life purpose?

39. What was the biggest mistake in history?

Mankind has made many mistakes. Which does he see as the worst?

40. How would you define “strength”?

Strength has many definitions, but what does he think it means to be strong?

41. Would you rather be a kid your whole life or an adult your whole life?

Does he long for the joys of youth or the wisdom of age?

42. What inspires you?

What pushes him to be a better man?

Downloadable and Printable List of Interesting Questions To Ask A Guy

Here is a downloadable and printable jpg/pdf list of interesting questions to ask a guy (right click the image and select Save Image As...):


How to Ask Interesting Questions To Ask A Guy

Asking interesting questions under the right conditions will help you make sure the next time you hang out with your friends is memorable. Follow these tips to make the most of your interesting questions.

Here's how to ask interesting questions to ask a guy:

1. Use context

Even questions as interesting as these can be hard to drop out of the blue. Try to include the questions naturally by choosing ones that are relevant to what's going on.

2. Make them your own

Think of these questions as a template that you can modify to fit yourself and your friends. Let your personality shine through!

More Best Questions To Ask

Check out some of these other posts for more of the best questions to ask, no matter the situation.

  1. These fun questions to ask will entertain a crowd.
  2. A few weird questions to ask can keep things interesting.
  3. Make better friends while you laugh using funny get to know you questions.

In Conclusion

Now that you've got a bunch of interesting questions to ask a guy you've got plenty to talk about next time you meet up with your friends.

Whether you're in the mood for something funny or something deep, you've got questions to ask in any situation.

So, lay off the small talk and use these questions to ask a guy about something that matters.