10 Essential Questions To Ask A Guy On A First Date

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First dates can be a mixture of excitement and nerves, but the right questions can turn small talk into a real connection. Instead of awkward silences or predictable chatter, why not ask something that sparks a genuine conversation? So, here are ten essential questions that go beyond the basics and will help you learn more about him while keeping things fun and engaging.

What’s Your Dream Adventure?

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This isn’t just about travel—it’s about how he sees the world. Some guys might light up at the thought of hiking through the Amazon, while others dream of road-tripping across the country in a vintage car. His answer will tell you if he’s spontaneous or someone who’d rather stay home and binge-watch Netflix.

What’s Your Go-To Comfort Movie?

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The movies and shows we love say a lot about us. Is he obsessed with action-packed thrillers? Does he rewatch “The Office” for the hundredth time when he’s had a long day? Not only does this question keep the conversation light and fun, but it also sets up a chance to bond over shared favorites.

What Skill Would You Want To Master Instantly?

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Everyone has something they wish they were naturally good at—playing the piano, speaking fluent Italian, cooking something more advanced than scrambled eggs. His answer can tell you a lot about his interests and ambitions without feeling like a deep, soul-searching question.

What’s The Funniest Thing That’s Ever Happened To You?

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This one is pure gold because it gives him a chance to tell a story, and nothing makes a first date more enjoyable than a good laugh. Plus, if he can laugh at himself, that’s always a green flag. Confidence is great, and someone who takes themselves too seriously can make a date feel like an interview.

What Are You Passionate About?

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You can learn a lot about a person by knowing what excites them. Maybe he’s passionate about photography, cooking, fitness, or playing the guitar. Whatever it is, hearing him talk about something he loves will give you a glimpse into what drives him. And if he struggles to come up with anything? That’s worth noting.

Do You Believe In Luck?

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Some people believe in destiny, while others think everything in life comes down to hard work. His answer might tell you whether he’s a realist or someone who carries a lucky coin in his pocket. If the conversation flows naturally, you might even find out more about his life philosophy—without it feeling like a TED Talk.

What’s Your Ultimate Comfort Food?

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It may sound simple, but food is personal. Maybe he has a soft spot for his grandma’s homemade lasagna or a childhood favorite like peanut butter and jelly. Talking about food is an easy way to keep the mood light, and if you two hit it off, it might even lead to a second-date idea.

What Do You Hate Most About The Dating Process?

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This one might come across as a bit of a shocker at first, but it’s something that is actually appreciated by a guy. That’s because, well, dating can be tough. There’s the whole deal of meeting someone, then talking to them, then feeling enough of something to take them out, and then actually meeting that person.

What’s One Bucket List Item You’re Determined To Check Off?

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Bucket lists are full of fun and wild dreams, so this question can bring out his adventurous side. Whether it’s skydiving, writing a novel, or backpacking across Asia, you’ll get insight into his long-term goals and personality. It’s also a great way to see how much of a go-getter he is.

Do You Have Any Pet Peeves?

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If you want to really find out what makes a person tick, ask them this. While the guy might appear to be cool, calm, and relaxed from the second you meet, as soon as you ask him this, he may completely change your opinion of him—in either a good or bad way.

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