45 Casual, Random Questions to Ask a Guy to Break the Awkward Silence

Have you ever been on a date and run out of things to say? Check out our list of random questions to ask a guy, and never suffer in awkward silence again!

No one ever says this, but dating is hard! But what is one of the hardest things about dating? That awkward lack of conversation. Cringe-worthy pauses ensue, and you don’t know any random questions to ask your guy that might break that awkward silence.

But what is the right thing you need to say? How do you kick off the conversation?

The answer is popping out some random questions to ask a guy. If you have some fun random questions in your back pocket at all times, the conversation will always flow effortlessly.

You’ll get him laughing, and thinking deeply. You’ll even get to know each other better. And best of all, you’ll have the perfect first date that leaves him desperate to come back for more.

So, let’s get started. This feature will show you the ultimate random questions to ask a guy, just in case things go quiet. [Read: 55 tips and tricks to leave your first date smitten & in awe!]

Here are some random questions to ask a guy

You want to keep the conversation going, so you’ll need to do your part and meet them halfway with engaging conversation. We know you’re nervous, we totally get it. But if you have some backup questions to throw out on the table, you’ll be much more at ease.

Here are some great random questions to ask a guy that can help cut the silence and ease the tension.

1. What’s your favorite outdoor activity?

Why not find out what they like to do in their spare time? Are they highly active or are they more like couch potatoes?

You may not see this as a big deal, but if he hates hiking, and you’re an award-winning mountaineer, this may be a little challenging. So try to match up your levels and styles of activity by asking this handy question.

2. How would you spend your dream weekend?

Would he want to be at the beach or laying in bed all day watching movies? Maybe he’d do some baking, or go do something crazy like skydiving.

Whatever he likes, make sure that it’s something similar to what you’d love to do. That way, if things work out, you can do it together! [Read: 60 deep & fun get-to-know-you questions to peek into their soul!]

3. What’s the craziest thing you’ve ever done?

Has he been skydiving? Scuba diving in the Great Barrier Reef? Asking this question is a great way to scope out his adventurous side and determine how much of a risk-taker he is.

Of all the random questions to ask a guy, this is one of the most revealing. Maybe he’ll tell you something that reveals an unexpected wild side!

4. If you could live anywhere in the world, where would it be?

Maybe he doesn’t want to live anywhere other than the city he’s in now, you don’t know! So if you’re an avid traveler, it’s a good random question to ask a guy.

Worst case scenario, you get together and find your future plans are completely incompatible, and that is actually really bad. So, find out now if he has the same dreams as you.

5. What’s your pet peeve?

Ask him this question and see if you two share the same one, or, even better, if you do everything that he can’t stand.

Pet peeves can end up being a real deal-breaker in a relationship; those tiny little things the other person does that you hate will mount up and cause resentment. On the other hand, griping about pet peeves can be very, very funny!

6. Kill, f*ck, or marry?

This one is just a fun random question to ask a guy. Name three people and see which one they would f*ck, kill, or marry.

Try asking him about celebrities, and then make things more dangerous by using people you both know. You can use people around you as well to make it more entertaining.

7. What’s your worst habit?

Right now, these might not get on your nerves, but if this relationship goes further, you’ll want to know these things!

Does he chew with his mouth open, leave the toilet seat up, or habitually stay up all night? [Read: 50 cute questions to ask a guy you like and catch his eye]

8. What’s your wildest travel story?

Is he even wild? Maybe he’s more into the resort life and usually opts for an all-inclusive break. Or is he too wild for you with his three-day weekend benders?

This is one of the random questions to ask a guy that shows where he stands on traveling and vacations. This could be the start of some crazy adventures together, so ask him!

9. What’s your favorite book?

This will show you if he even reads at all. If he reads anything other than his emails, he’s a keeper. But best case scenario, he loves to read and has tons of interesting books to recommend.

You could end up talking for hours about all the fascinating stories he’s found between their pages. Perhaps you’ve read some of them already, so you can discuss them together.

10. Can you dance?

Yeah, well, this is important. If he says yes, then ask if he can dance well. Because at the end of the day, women like men who know how to move their feet. 

If a guy’s good on the dancefloor, he’s usually good in bed, if you don’t believe us then find out for yourself! [Read: 156 sexy, dirty questions to ask a guy & make him horny just listening to you]

11. What are your political views?

There’s an old rule that says don’t discuss religion or politics on a first date. We know this could end up making or breaking the date, but screw it!

It’s going to come up at some point, so why not get it out of the way now? If you’re both on two ends of the stick, well, have fun on the rest of that date!

12. What’s the worst date you’ve been on?

Everybody has a story. If they’ve ever used Tinder, they have a story… or five. So give him an opportunity to crack you up with his tragic dating stories. Plus, it’s a great way to have a good laugh and share your experience of dating.

13. Biggest turn-off in a woman?

This doesn’t mean you have to change who you are. Just because he doesn’t like it when a woman snorts when she laughs doesn’t mean you have to change the sound of your natural giggle.

But it’s interesting to see if his turn-offs are more appearance-based or not.

This question will really reveal whether or not he’s shallow. [Read: 26 things to talk about on a first date to make them like you instantly]

14. Do you like animals?

If you’re a hardcore animal lover, and he can look at a picture of a dog and just say “meh,” then you might want to run for the door. This random question to ask a guy is fun and light-hearted, but it can also reveal a big deal-breaker for either of you—two birds and one stone!

15. What superpower would you have and why?

Is it X-ray vision? Is it telepathy? Ask them why they chose what they did. Perhaps they’re a massive Marvel fan; this will kick off a conversation about your favorite superhero movie. Marvel or DC? There’s another great random question to ask a guy!

16. Boxers or briefs?

You came here looking for random questions, so why not ask this one? Plus it helps build the fantasy in your head. [Read: 196 fun & deep relationship questions to test your couple compatibility]

17. Morning or night person?

Maybe he’s a night guy and you’re a morning girl. Nothing wrong with that, but you two will just need to compromise. Find out if he loves to go for jogs in the early morning, or loves to stay up all night watching movies.

If you get together, this could be a great opportunity to change your routine.

18. Show me your best accent

This is just for laughs because it’s always a fun random question to ask a guy. Get him to show you his best impression of a worldwide accent. He might be amazing at it, or he might be awful; either way, it’ll be hilarious!

However, this can turn very racist very quickly. So make sure you call him out if this question exposes him as a bigot.

19. What’s your dream job?

Is he living his dream job? Why not? Ask him what his ideal job would be, and interpret his answers. Of course, he might not want to have a job at all; his dream might be something more creative or based on travel.

Whatever he dreams about, talking about dreams is always the start of a super romantic conversation.

20. How do you feel about the five-second rule?

If he sees you eating popcorn off the floor, will he applaud you or look at you in disgust? How picky is this guy?

Although this might seem like a silly random question to ask a guy, it tells you a lot about his hygiene. Nobody wants to date a guy who wallows in his own filth… unless you’re a little gross too!

[Read: Getting the answers you crave: 30 questions to ask a guy]

21. What kind of drunk are you?

If he’s an angry drunk, he clearly has some issues. That’s a clear red flag that might mean it’s time to leave, or at least stop buying him any more drinks.

So, this question is a good way to spot a potential personality problem without having to ask something overly serious.

22. What’s your favorite movie?

What kind of movies does he watch? What is his favorite movie genre? These are all important, albeit random, questions to ask a guy because you might very well be cuddling together for a Netflix and Chill sesh soon!

23. Where’s the craziest place you’ve had sex?

Here we go, let’s see how naughty this guy is. We all have a kinky side… has his been shown yet? Use this question to find out if he’s a Christian Grey or more straight-laced. [Read: 100 juicy, sexual questions to ask friends & have a fun, naughty time]

24. Have you ever been cheated on?

Has he ever had to deal with a cheating partner? How did he cope? Or better yet, has he ever cheated on someone?

He may not be honest with you on it, but it’s worth asking. Especially if you’re into this guy and planning a long-term committed relationship.

25. What do you love the most in bed?

Blowjobs? Anal sex? Giving head? What does he get turned on by the most? This might be more of a dirty question to ask a guy, but it’s a great one to have on hand if you want to heat things up. If you ask this right, it could be your cue to head home… together! [Read: 150+ personal questions to ask a guy to get him to open up to you]

26. Have you ever been in love?

If he’s 35 years old and has never been in love, something is definitely up. This is one of the really good random questions to ask a guy as it may reveal a red flag or two. It lets you know how quickly he falls in love, too.

Things could get way too intense if he’s fallen in love five times this year already so yeah, we recommend asking him this question.

27. What do you wear to bed?

Well… is he a birthday suit kind of guy? Does he sleep in his undies? Or maybe he’s down to wear matching PJs with you? You can tell a lot about a guy by finding out what he wears to bed.

Furthermore, this is a great one to pair with the question about what he likes in bed.

28. What do women compliment you on the most?

We like this question because you get to see what they think of themselves, and how people see them. Does his self-image match what you see?

Ask a guy this random question so that you can find out the status of his self-esteem. Does he know how good-looking *or not* he is?

29. Have you tried online dating?

Nowadays, lots of people meet through online dating. But maybe you actually are on this first date thanks to your mom. So, not a bad question to ask if you didn’t meet on Tinder. Find out if he’s got a long history online, or if he prefers to search for love IRL. [Read: 40 things to ask a guy that’ll leave him crazy about you]

30. What’s your favorite breakfast to have in the morning?

You know, just in case he spends the night. If you do end up spending the night together, you can surprise him by making his favorite dish when he wakes up.

It’s like something out of a rom-com, right? Of course, he could also be a weirdo who eats raw meat for breakfast or something like that.

31. What is the weirdest reason you’ve ever broken up with someone?

Some people break up with partners for the weirdest reasons. Maybe they don’t like the sound of them chewing, the way they smell, or even the way they talk.

If the guy you’re dating has broken up with somebody for a weird reason, he might break up with you for a weird reason too, so it’s good to know in advance.

32. When was the last time you laughed the hardest?

Humor is one of the sexiest things about a guy. So, ask him what he finds funny. Maybe you had to be there, but most of the time hearing about a funny event is just as hilarious as watching it play out in real-time. Plus, if he can make you laugh, that’s hot.

33. If you could listen to only one song for the rest of your life, what song would you choose?

What’s his music taste like? Does he like the same artists as you? Music is well known to be the food of love, so get that love flowing by finding out his favorite song.

What song would he choose if there were no other songs in the world? [Read: How to end a date the right way without feeling awkward]

34. What celebrities have you met?

How close has he got to fame? Perhaps he’s met a famous person, or even has some stars in his family. Celebrity culture is always fun to gossip about, so get the conversation going by chatting about your favorite celebs.

Of course, if you’re not interested in celebrities, this will also help you find out if he feels the same way.

35. What word do you hate?

Moist. Guesstimate. Crevice. Feel uncomfortable yet? All of these words often come up as the most hated words in English. What word does your date hate?

This might seem like a random question to ask a guy, but it could tell you a lot. Maybe he hates the words ‘bae’ or ‘wifey’—if you like to hear those names, you’re probably not compatible.

36. What is your pop culture guilty pleasure?

Does he never miss an episode of Keeping Up With The Kardashians? Or, has he got big love for Big Brother? Maybe he even likes to shake it to Lizzo when he’s alone in his room.

Whatever it is, his pop culture guilty pleasure is always a super fun thing to talk about on a date, so make sure you ask him. It might show you a hidden side of him, too.

37. What is the most embarrassing thing that ever happened to you?

Everybody has some mildly traumatic embarrassing memories locked up deep down in their head. Ask him what keeps him cringing when he’s trying to get to sleep at night.

Usually, it’ll be something hilarious! Make sure you offer your embarrassing story too though, so he doesn’t feel like he’s the only one under the spotlight.

[Read: 23 first-date conversation tips to impress your date in minutes]

38. What is the weirdest thing you’ve ever bought?

Online shopping is a dangerous thing. We’ve all got drunk and ordered some crazy item, or made some bad fashion choices when shopping late at night.

So ask your date what’s the weirdest thing he’s ever bought. It might tell you about a strange hobby he’s got. This question can also tell you about his attitude to money.

39. Have you ever been to a palm reader?

Of all the random questions to ask a guy, this is one of the weirdest. However, asking your date about his supernatural experiences is a great way to start a conversation about spirituality.

Also, if he has seen a fortune teller, you might be able to find out his star sign. You can learn a lot about your compatibility by comparing your charts.

40. Who would you rather hire: a personal trainer, a personal chef, or a housekeeper?

Hopefully, he’s rich enough that he’s already hired all three. However, if he isn’t a multi-millionaire, it’s interesting to know what he *would* spend his riches on.

Would he prioritize being healthy, or keeping a presentable showhome? Or, would he pig out on luxury meals? [Read: 18 signs your date likes you and wants to see you again ASAP]

41. What’s the most dangerous experience you’ve ever had?

Has he ever been close to death? When has he felt most afraid? Of course, he might be an adrenaline junkie who performs death-defying feats for fun. But if he’s a mere mortal, it’s interesting to find out which risks he’s been willing to take in the past.

Also, whether these were in the name of helping others, overcoming his fears, or just sheer thrills.

42. Planes, trains, or automobiles? How do you prefer to travel?

Does he like to use public transport, or does he have his own car? If he likes to travel by car but doesn’t have a vehicle, you could end up driving him everywhere. Or if he’s afraid of flying, that could mean more staycations are on the horizon.

43. How much time do you spend getting ready in the morning?

Are you a girly girl? When a girl who likes makeup dates a guy who likes grooming, they can end up having some serious fights for the bathroom. So, ask a guy this random question to find out if he’s a 10-minute kind of man or a bathroom hogger like you.

You can also find out how vain he is. If a guy spends four hours a day getting ready, that’s a sign he’s seriously self-absorbed. [Read: 30 first date rules for guys and girls that’ll make your date adore you]

44. What’s something kids today have you wish you had growing up?

The experiences we have growing up shape our personalities for the rest of our lives. So, ask your date about his early life. Is there a toy, gadget, or trend kids have today that makes him jealous? This random question will show you what he was like as a kid. That could be seriously cute, right?

45. Android or Apple?

The most important question of our age. You probably already know from the color of his message bubbles. But would he ever cheat on his current phone company with the other side?

What should you know before asking a guy random questions?

So, now you know the ultimate random questions to ask a guy. But is it ever a bad idea to ask a guy random questions? You don’t want to make him feel like he’s being interrogated—this isn’t Guantanamo Bay.

[Read: The dangerous signs you’re accidentally ruining your first date]

Also, you don’t want to ask him wrong and get crappy answers. So, what should you be mindful of before you start firing off those questions? Here are our top tips:

Never interrogate him

It’s possible that he won’t feel comfortable answering some of these questions. There are lots of reasons why he might not want to talk about his childhood, for example; maybe he went through abuse, came from a broken home, or just didn’t have a happy youth.

So, you need to be careful that you don’t upset your date when you’re asking questions, and be sensitive to his feelings.

If he doesn’t want to answer a question, there is one magical thing you can do to keep him happy and safe. That’s right—just change the subject. There are so many other things you can talk about, and so many other random questions he can answer.

After all, it’s no fun if he’s upset. Instead, hit him with a question that’ll actually make both of you smile.

Have an arsenal of tricky and baffling questions!

Asking questions is also no fun if the questions are too easy. There’s a reason why our random questions to ask a guy cover a huge range of weird and wonderful topics. The more out there your question is, the more surprised he’ll be when he’s asked it.

So, keep your questions unexpected. Go for the weirdest, toughest, craziest questions you can imagine. If you can’t imagine them, then just pick some out from our ultimate list! [Read: 42 flirty first date tips for girls to leave a guy wanting more]

Be ready that a question might backfire

Of course, when you ask a question, you have to be prepared for the answer. There’s a possibility that you won’t like what you hear.

The answers he gives might tell you that you’re incompatible, or that you don’t actually know him the way you thought you did. But don’t assume he’s a catfish; he hasn’t turned into a different person. Everything you find out about him through these questions was already there when you met him, it just wasn’t visible up to now.

So, if you find out something unexpected, it’s not a bad thing. It’s a good thing! You would’ve found out those answers anyway.

However, if you ask those tough questions early, you won’t have to go through the pain they might cause later. It’s much better to be disappointed early than to make a long, hard mistake.

Now that you have a couple of different random questions to ask a guy in your back pocket, you’ll be able to whip one out when the crickets start chirping. So get out there and have the best date ever!