30 Random Questions to Ask a Guy and Break the Awkward Silence

First dates are awkward enough as it is. So, if you’re on one, you want to have some random questions to ask a guy, just in case things go quiet.

random questions to ask a guy

I’ve been on so many dates, I can’t keep track anymore. Obviously, most of those never made it past the first one. I’d like to say it’s because of them, but it’s probably because I love eating with my hands. Whatever… sue me. But aside from them staring at me in horror, I had some really good random questions to ask a guy.

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 in conversation. I know you’re nervous… I totally get it. But if you have some backup questions to throw out on the table, you’ll be more at ease. Once you have a couple questions sitting in your back pocket, it’ll be a breeze. 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.

#2 How would you spend your dream weekend? Would he want to be at the beach or laying in bed all day watching movies? [Read: 60 get to know you questions for a new romance]

#3 What’s the craziest thing you’ve ever done? Has he been skydiving? Scuba diving in the Great Barrier Reef? This is a great way to scope out his adventurous side and determine how much of a risk-taker he is.

#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 question to ask.

#5 What’s your pet peeve? Let’s see if you two share the same one, or even better if you do everything he can’t stand.

#6 Kill, f*ck, or marry? This one is just fun. Name three people and see which one they would f*ck, kill, or marry. You can use people around you as well to make it more entertaining.

#7 What’s your worst habit? If he chews with his mouth open, my God, you’re not going to last. Those squishy sounds are gross… ugh. Yeah, get this out of the way ASAP. [Read: 50 cute questions to ask a guy you like to catch his eye]

#8 What’s your most wild travel story? Are they even wild? Are they more into the resort life or are they too wild for you? This is one of the random questions to ask a guy that kind of sees where they stand on travelling and vacations.

#9 What’s your favorite book? This will show you if he even reads. I know, baby steps, baby steps. If he reads anything other than Facebook, he’s a keeper.

#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, we women like men who know how to move their feet. [Read: 20 sexy questions to ask a guy to seduce him]

#11 What are your political views? I know this could end up making or breaking the date, but screw it! It’s going to come up at some point. You’re for Obama and he’s for Trump, haha, well, have fun on the rest of that date.

#12 What’s the worst date you’ve been on? They have a story. I mean, if they’ve ever used Tinder, they have a story… or five. Plus, it’s a great way to have a good laugh and share horror stories.

#13 Biggest turn off in a woman? This doesn’t mean you have to change who you are because they don’t like it when a woman snorts when she laughs. But it’s interesting to see if his turn offs are more appearance-based or not.

#14 Do you like animals? If he doesn’t, he’s not wanted. I mean, how can you not like animals? His only excuse is if he’s allergic, other than that, he’s a psycho.

#15 What superpower would you have and why? Is it X-ray vision? Is it telepathy? Ask them why they chose what they did.

#16 Boxer or briefs? Umm… because why not ask this question? Plus, it helps build the fantasy in your head. [Read: 50 relationship questions to test your compatibility instantly]

#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.

#18 Show me your best accent. I mean, this is just for laughs and it’s always fun to ask.

#19 What’s your dream job? Is he living his dream job? Why not? Ooh, the plot thickens.

#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? I mean, how picky is this guy? [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. So it’s a good way to sport a red flag without having to ask something overly serious.

#22 What’s your favorite movie? Who knows, maybe they have lame taste in films. If that’s the case, your movie nights aren’t going to be that great.

#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? [Read: 36 racy and flirty questions for naughty girls and guys]

#24 Have you ever been cheated on? 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.

#25 What do you love doing in bed? Blowjobs? Anal sex? What does he get turned on by the most? [Read: 17 personal questions to ask a guy to get the inside scoop]

#26 Have you ever been in love? If he’s 35 years old and never been in love, something is definitely up. This is one of the really good “red flag” random questions to ask a guy.

#27 What do you wear to bed? Well… is he a birthday suit kind of guy? Or maybe you two have matching PJs.

#28 What do women compliment you on the most? I like this question because you get to see what they think of themselves and what people see. Does it match what you see?

#29 Have you tried online dating? 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.

#30 Your favorite breakfast to have in the morning? You know, just in case he spends the night.

[Read: 40 things to ask a guy that’ll leave him crazy about you]

Now that you have a couple different random questions to ask a guy in your back pocket, you’ll be able to whip one out when the crickets start chirping. But, that’s not gonna happen.

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Natasha Ivanovic
Natasha Ivanovic is an intimacy, dating, and relationship writer best known for her writings on Kiiroo, LovePanky, Post Pravda, and more. She's the creator and ...
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