85 Interesting, Random Questions to Ask a Guy to Break the Awkward Silence

You’re talking to a guy and… you run out of things to say. Yikes, right? With these random questions to ask a guy, you’ll never run into awkward silences!

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 interesting and random questions to ask your guy that might break that awkward silence.

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!]

The best interesting and random questions to ask a guy

You want to keep the conversation going, so you’ll need to do your part and meet him halfway with an 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 he likes to do in his spare time? Is he highly active or is he more like couch potatoes?

You may not see this as a big deal, but this may be a little challenging if he hates hiking and you’re an award-winning mountaineer. 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 lying 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 interesting and random questions to ask a guy, this is one of the most revealing.

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. 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! [Read: 20 annoying things it’s okay to hate about your partner]

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 he would f*ck, kill, or marry.

Try asking him about celebrities, and then make things more dangerous by using people you both know.

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 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 the 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 he’s ever used Tinder, he has 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 him why he chose what he did. Perhaps he’s 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: Boxers or briefs – what girls like, pros, cons & how to tell what works for you]

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!

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.

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 – 108 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 interesting question to ask a guy 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 interesting and 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?

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 interesting question to ask a guy because you get to see what he thinks of himself, and how people see him. 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’re 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! [Read: 17 good & bad types of humor and how they affect your relationship with others]

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?

34. What celebrities have you met?

How close has he gotten 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. [Read: 23 first-date conversation tips to impress your date in minutes]

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.

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

Online shopping is a dangerous thing. We’ve all gotten 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 interesting question to ask a guy can also tell you about his attitude to money.

39. Have you ever been to a palm reader?

Of all the interesting and 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 home? 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?

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.

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 that 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? This interesting question to ask a guy can tell you a lot more about him than you might think!

46. What was your best drop-the-mic moment?

Ah, this one’s gold for tapping into his sense of accomplishment and self-esteem. Who doesn’t love to share that time they absolutely crushed it? It reveals not just what they’re proud of, but also what they value as a mic-drop-worthy moment.

If his answer is about nailing a work presentation, he may be career-focused. If it’s about a personal relationship, his priorities may lie closer to home.

47. What childish thing do you still enjoy?

Welcome to the world of the “inner child,” a psychological concept that taps into our most basic and free-spirited experiences. This interesting question to ask a guy is a beautiful way to explore someone’s softer, more whimsical side.

Plus, it’s a great compatibility check. If he loves building LEGO sets and you love smashing them, well, you’ve got a fun day ahead!

48. What’s the biggest doubt you have?

Oof, this one dives deep into the abyss of insecurities and fears, doesn’t it? Everyone has doubts, and admitting them can show a level of self-awareness and vulnerability.

This is rich territory for exploring one’s “shadow self,” that hidden, darker part of our personality that Jung talked about. [Read: Overcoming self-doubt – 26 signs & best ways to stop doubting yourself]

49. Who has completely lost your respect?

This question explores values and ethical boundaries. Losing respect for someone usually indicates a clash of principles or expectations, and this can reveal a lot about a person’s moral or ethical compass.

50. What movie do you wish life was more like?

Talk about “narrative identity,” a theory suggesting that we make sense of the world and ourselves through stories.

Does he wish life was more like a Marvel movie, filled with heroes and action? Or perhaps a rom-com? Either way, you’ll get a glimpse into how he views the world or wishes to view it.

51. How many phones have you broken or lost?

This is an interesting question to ask a guy because it offers a sideways look into responsibility and lifestyle. If he’s never lost or broken a phone, he’s likely cautious and responsible. If he’s lost count, well, he might live life on the edge—or he’s just really clumsy.

52. What is the most useless thing you know how to do?

This is a fun way to explore someone’s quirky talents or weird knowledge. Who knows, maybe he can solve a Rubik’s Cube with his toes?

This taps into the idea of “useless skills,” which, contrary to their name, often make us unique and memorable.

53. What’s the worst and best thing about being male?

Ah, a gender-norm challenge! This one brings in elements of social psychology by exploring how societal norms and expectations shape our experiences.

Also, it’s a chance to delve into the pros and cons of traditional masculinity. A thoughtful answer could show high emotional intelligence. [Read: What makes a man a man – 20 manly & relevant traits that defy stereotypes]

54. If you could learn only one magic spell, but it could only do something mundane and boring, what would the spell do?

This is a quirky and interesting question to ask a guy that explores practicality within the realm of fantasy, tapping into both creativity and real-world needs.

Does he want a spell to always find matching socks? Or maybe he’d like a spell for instant coffee? This is essentially asking about the small, mundane inconveniences that bug them.

55. What would be the consequences of a scientific discovery that extended the lifespan of humans to 500 years?

Oh, we’re delving into the bioethical implications here! This one taps into opinions on science, morality, and even overpopulation.

It’s not just for sci-fi nerds but also for anyone who loves to ponder the “what-ifs” of our world. He could bring up everything from resource scarcity to the psychology of immortality.

56. What’s the best prank you can play on someone?

Tapping into someone’s sense of humor, especially through pranks, offers a look into their creativity and boundaries.

If his prank is elaborate, he might be a strategic thinker. If it’s innocent and funny, he might value lightheartedness.

57. What would be the worst thing to have a phobia of?

Fears and phobias are grounded in our primitive “fight or flight” instincts. Identifying the worst possible phobia can be a window into what a person finds indispensable in their life, like social connections or even technology. [Read: 20 downright strange but true phobias about love]

58. What could you give a thirty-minute impromptu lecture on?

Intriguing! This question reveals where someone’s expertise or strong interests lie. Whether it’s the intricacies of craft beer or the philosophy of Kant, you learn what really fires him up.

59. What do you own that a lot of people comment on?

Uncover what stands out about him with this query. Is it a tattoo with an amazing backstory, or perhaps a unique piece of jewelry?

Items like these often serve as social markers, sparking conversations and revealing aspects of personality.

60. What game do you always lose at?

This random question to ask a guy digs into his competitive nature and humility. Admitting defeat in something as simple as a game can show a willingness to be vulnerable and honest. [Read: 22 super fun drinking card games to get the party & fun times going]

61. What’s your go-to karaoke song, and why?

Karaoke is the playground of hidden talents and not-so-secret passions. This question might reveal whether he’s a romantic at heart or a retro enthusiast who loves to rock out to ’80s classics.

62. How do you handle stress?

Stress management is integral to mental well-being. Whether he leans more towards “fight” or “flight” could reveal his default coping mechanisms, be it confrontational or avoidant.

Understanding if a guy is confrontational *fight* or avoidant *flight* when stressed can offer you an invaluable preview of how he might deal with conflicts or crises in a relationship.

For example, if he leans more towards “fight,” he may be the kind who wants to tackle relationship issues head-on, never shying away from difficult conversations. On the other hand, if he leans more towards “flight,” he might need space and time to process problems, potentially leading to periods of emotional distance before a resolution is reached.

63. If you could have dinner with any historical figure, who would it be and why?

An oldie but a goodie among interesting questions to ask a guy! This taps into his historical interests and what qualities he values in leadership or innovation.

64. If your life were a movie, what would its title be?

Invite him to sum up his life in a few words. This question can be revealing and foster deeper conversation about life goals, experiences, and personal narratives.

Will the title he picks be something whimsical like “The Eternal Optimist: A Tale of Unbridled Enthusiasm and Suspiciously Sunny Weather,” or perhaps something more contemplative like “The Search for Meaning: Now Playing in a Midlife Crisis Near You”?

65. How do you define success? *Intrinsic vs. extrinsic motivation, anyone?*

A cornerstone question in the realm of psychology. Is he driven by internal factors like personal growth, or does he lean on external rewards? The intrinsic vs. extrinsic motivation debate comes into full view here.

66. What’s the most recent show you binge-watched and loved?

A casual way to understand his tastes while also getting good Netflix recommendations. It’s a win-win! [Read: 69 best & most romantic movies that are a must-watch in 2023]

67. What’s the one thing you’d save in a fire, aside from humans and pets?

This question often highlights a person’s priorities and what they find irreplaceable—whether it’s sentimental or practical.

So, will it be his limited-edition Star Wars action figures or his cherished childhood photo album? Maybe it’s something super practical, like his laptop, revealing a utilitarian side.

This isn’t just one of those random questions to ask a guy, it’s a sneak peek into what he values beyond the obvious. Knowing what he’d rush to save as the metaphorical *or literal* flames dance around him could tell you a lot about where his heart truly lies.

68. What’s a skill you’re terrible at but wish you had mastered?

Have you ever heard of the Dunning-Kruger effect? This effect is about people overestimating their abilities. Here, he gets to admit his limitations, possibly revealing a humbler or more self-aware side.

69. What’s your spirit animal and why?

This offers an entertaining way to explore someone’s traits or characteristics they admire in animals, whether it’s the loyalty of a dog or the independence of a cat.

70. What’s your love language?

Love languages are a powerful tool for understanding how someone likes to give and receive affection. [Read: Words of affirmation – how to use it, 56 signs, tips & examples to say it right]

If he’s all about words of affirmation, then you’ll know your text messages and heartfelt conversations will go a long way in strengthening your relationship. On the flip side, if his love language is Physical Touch, then a hug or a kiss could speak volumes more than any poetic verse.

71. Are you an introvert, extrovert, or ambivert?

Dive into the psychology of social interactions. Knowing someone’s social comfort zone can help predict compatibility in various settings.

72. What’s your signature dance move?

Hilarious and telling! Is he a reserved two-stepper or the king of the moonwalk? This is both an interesting and random question to ask a guy to gauge his sense of fun. And hey, if he’s got some slick moves, maybe you could even ask him to teach you!

That would not only be a super fun date idea, but it’s also a sneaky way to gauge how patient and communicative he is—two essential traits for any budding romance.

73. What’s a strange food combo that you love?

Tastes can be an oddly personal topic. Whether it’s fries dipped in ice cream or pickles with peanut butter, you’ll learn about his unique *or questionable* culinary preferences.

74. What’s a personality trait you admire in others?

It could be altruism, or it could be wit! Delve into the characteristics that he values in other people. Whether he appreciates the kindness of altruism or the quick thinking of wit can tell you a lot about what he strives to be.

75. Do you believe in fate or free will?

Discussing fate versus free will isn’t just intellectual banter, it can also hint at how someone approaches life and relationships. [Read: 30 deep, thought-provoking questions that’ll leave you curious & wondering]

Does he believe in making his own destiny, or does he think some things are simply meant to be? This can influence how proactive or passive he might be in a relationship.

76. What’s your favorite meme?

Memes are digital shorthand for a myriad of emotions and cultural nuances. Knowing a guy’s favorite meme can provide insights into his sense of humor and his level of engagement with pop culture—both of which could be significant in a dating context.

77. What fictional world would you love to live in?

This interesting question to ask a guy moves beyond fantasy to tap into ideals and preferences.

Whether he chooses a world rich with magic or one grounded in stark reality, it can indicate what kind of escapism he leans towards and how that could translate into your real-world experiences together.

78. Who was your first celebrity crush?

Knowing someone’s first celebrity crush could potentially reveal initial ideals or attributes they find attractive. It’s a lighthearted yet insightful way to understand his early impressions of romance and attraction.

79. If you had to perform in a talent show, what would you do?

This question uncovers hidden skills or passions that may not be immediately obvious. From a dating standpoint, these talents could be potential activities you can enjoy together. [Read: 196 fun & deep relationship questions to test your couple compatibility]

80. What’s your biggest “what if” in life?

The “what if” question probes into regrets or missed opportunities, illuminating his propensity for risk-taking. In a relationship, this could manifest as either cautiousness or adventurousness.

81. What’s a conspiracy theory you kinda, sorta believe?

Unpacking this question can disclose his level of skepticism and how much he questions conventional wisdom. It’s good to know if you’re dating someone who takes everything at face value or critically evaluates information.

82. What’s the most valuable lesson you learned from a mistake?

This interesting question to ask a guy is a pathway to understanding his approach to personal growth and how he handles setbacks, which are inevitable in any romantic relationship.

83. Do you think humor is a sign of intelligence?

This topic dives into his view on the interconnectedness of humor and intellect. A sense of humor often plays a key role in relationship compatibility. Witty banter = cortical fireworks! [Read: Witty banter – what it is & 15 secrets to talk witty & make people laugh]

84. What’s the craziest dream you’ve ever had?

Our dreams often mirror our subconscious. Understanding his wildest dreams can reveal hidden fears or desires that he might not openly discuss but are important to know in a relationship.

85. What’s your guilty pleasure food?

Comfort food choices can be revealing in their own way, opening a discussion about indulgences and how he treats himself, which can be valuable in understanding how he might treat a partner.

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.

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

1. Never interrogate him

It’s possible that he won’t feel comfortable answering some of these questions. 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.

2. 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]

3. 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.

[Read: 34 secrets to get a man to open up, communicate & understand you better]

With these 85 interesting and random questions to ask a guy, you’ll never run out of things to say! So face that awkward silence with these conversation starter questions and get to really know him!