21 Questions to Ask a Guy: Get to Know Him on a Deeper Level

Let’s be real: small talk can only get you so far. You can chat about the weather, favorite pizza toppings, or the last show you binge-watched—but at some point, you want to really know the guy you’re talking to.

That’s where the right questions come in.

Whether you’re just getting to know someone or you’ve been dating for a while and want to deepen your connection, asking meaningful, fun, or even flirty questions can be the spark that turns a casual conversation into something way more exciting.

And no—we’re not talking about awkward job-interview vibes or anything that feels like a pop quiz.

We’re talking about real, thoughtful, and sometimes hilarious questions that open the door to deeper conversations, better connections, and maybe even a little romance.

So if you’re ready to take your chats to the next level, here’s a list of 21 questions to ask a guy—complete with tips, insights, and a breakdown of why each one matters.

Why Asking the Right Questions Matters

Think about the best conversations you’ve ever had. Chances are, they weren’t just about facts—they were about feelings, ideas, dreams, and shared laughs. The right question can:

• Break the ice in a fun, effortless way
• Reveal shared values or interests
• Build trust and emotional intimacy
• Help you figure out if you’re compatible

When you’re getting to know a guy, asking the right mix of lighthearted, personal, and deep questions helps move things past surface level and into real connection territory.

Let’s break it down into 21 powerful, playful, and insightful questions.

21 Questions to Ask a Guy:

1. What’s something you’ve always wanted to try but haven’t yet?

This question taps into his adventurous side and gives you a peek at his bucket list. Maybe it’s skydiving. Maybe it’s learning how to surf. Maybe it’s just trying sushi for the first time. Whatever it is, it opens the door to a convo about dreams and taking chances.

Pro Tip: You can follow up with, “What’s been stopping you?” to learn more about his mindset and priorities.

2. What was your favorite childhood memory?

A little nostalgia never hurts. Childhood memories reveal a lot about someone’s upbringing, values, and what made them smile before life got complicated. Plus, it’s just sweet.

Why it works: You’ll get to see his softer side and maybe even laugh over shared childhood experiences (hello, tree forts and cereal obsessions).

3. What’s your go-to comfort movie or TV show?

This is a fun, low-pressure question that gives you insight into his personality. Is he a “The Office” rewatch kind of guy? A Marvel superfan? A sucker for rom-coms (don’t laugh—it happens!)?

Bonus points: Ask why he loves it. Nostalgia, comedy, or a favorite actor could be the reason.

4. What’s something most people don’t know about you?

Time to get personal. This question encourages vulnerability—but in a subtle, safe way. You might learn something surprising, silly, or even profound.

Why it works: It shows you care about the real version of him, not just what he puts on display.

5. If you could live anywhere in the world for a year, where would you go?

This question combines imagination and lifestyle goals. Whether he picks a beach in Bali, a loft in New York City, or a cabin in the mountains, you’ll learn what kind of environment lights him up.

Fun follow-up: “What would you do there?”

6. What does your perfect weekend look like?

This helps you understand his vibe. Is he outdoorsy? A homebody? Someone who lives for brunch and Sunday football? You’ll get clues about your compatibility and shared interests.

Why it matters: Knowing how someone relaxes is just as important as knowing how they hustle.

7. What’s one thing you’re super passionate about?

Passion is attractive. Whether it’s music, fitness, gaming, or photography, learning what lights a guy up will bring out a whole new side of him. Watch his face when he starts talking about it—you’ll see.

Pro Tip: If you’re genuinely curious, ask him to show you or teach you something about it.

8. What’s something you’ve learned the hard way?

Okay, this one’s a little deeper—but it can reveal a lot about resilience, lessons, and how he deals with life’s curveballs. It also creates space for honest storytelling.

Heads-up: Be gentle and don’t force a deep answer if he’s not ready. The idea is to invite honesty, not pressure him.

9. What’s your love language?

This is lowkey one of the most important questions, especially if things are starting to get romantic. Knowing how he gives and receives love helps both of you show up better in a relationship.

Bonus Tip: If he doesn’t know, you can explain the five love languages—it’s a fun way to learn about each other.

10. What’s your biggest dealbreaker in a relationship?

It’s bold—but important. You don’t want to invest time in someone only to realize your values clash. This question can also show maturity and emotional awareness.

Why it matters: Knowing his boundaries is just as important as knowing his dreams.

11. What’s one thing you’re really proud of?

This is a confidence-boosting question that lets him share a win. Maybe it’s a project at work, running a marathon, or even helping someone through a tough time. Celebrate his wins—it brings out the best in him.

12. Do you believe in soulmates?

This one’s dreamy, and yeah—it can get pretty romantic. You’ll quickly find out if he’s a realist, a romantic, or somewhere in between.

Bonus points: Share your own views, too. It can lead to some surprisingly honest exchanges.

13. What’s your biggest fear?

A little vulnerability goes a long way. Whether it’s fear of failure, losing someone close, or something more abstract like not living up to his potential, this kind of question builds trust.

Keep it safe: Let the convo flow naturally. Don’t push if he’s not ready to open up fully.

14. If money weren’t a factor, what would you do with your life?

This is a dreamer’s question. It gives insight into his passion, purpose, and what he really wants to do—not just what he’s currently doing.

Fun twist: Ask him to describe his “dream day” in detail.

15. What’s one thing you wish more people understood about you?

This one’s deep and can uncover hidden layers. It’s a gentle way of asking, “What don’t people see when they look at you?”

Why it works: Everyone wants to feel seen. This question helps you do just that.

16. What’s your idea of a perfect date?

Whether you’re planning one or just curious, this question reveals his romantic style. It also gives you ideas for future plans. Win-win!

Pro Tip: If he turns the question back on you—answer honestly!

17. Who has had the biggest influence on your life?

This question brings up gratitude, role models, and formative moments. It could be a parent, a coach, a friend, or even a celebrity.

Why it’s good: You’ll learn what he values most in people—and maybe even how he sees himself.

18. How do you handle stress?

Life isn’t always sunshine. How someone handles stress says a lot about their emotional intelligence and coping skills. This question opens the door to talk about mental health in a chill, non-judgy way.

Follow-up: “What helps you recharge when you’re feeling overwhelmed?”

19. If you wrote a book, what would it be about?

This one’s creative and unexpected. Whether he imagines a novel, a memoir, or a book of funny stories, you’ll learn more about his imagination and interests.

Bonus twist: Ask him what the title would be!

20. What’s the best compliment you’ve ever received?

We love this one because it’s confidence-boosting and revealing. Compliments often highlight what others see in him—and what he secretly values about himself.

21. What does happiness mean to you?

Let’s end on a big one. Happiness looks different for everyone. Some guys crave success. Others want peace. Some dream of family life. Whatever his answer, it’s a window into what really matters to him.

Tips for Asking These Questions

Asking great questions is only half the magic—the other half is how you ask them. Here’s how to keep it smooth and natural:

• Start light: Don’t dive into super personal stuff right away.
• Be present: Listen fully. Don’t plan your next question while he’s talking.
• Be playful: A flirty smile and a “your turn to answer!” keeps the convo fun.
• Share your answers too: Vulnerability builds connection when it goes both ways.

Frequently Asked Questions

1. When is the best time to ask these questions?

The best time is when the vibe feels relaxed and open. Think chill conversations during a walk, over dinner, or late-night texting sessions. Avoid bombarding him all at once—sprinkle the questions naturally over time.

2. Are these questions good for a first date?

Absolutely! Just start with the lighter ones (like favorite childhood memories or dream travel spots) and save the deeper ones (like fears or love languages) for later. Keep it easy and fun.

3. What if he doesn’t want to answer one of the questions?

That’s totally okay. Respect his boundaries and move on to another topic. Sometimes people need time to open up—and forcing a deep convo never leads to real connection.

4. Can I ask these questions over text?

Yes! Some of these questions work great over text or even on dating apps. In fact, questions like “What’s your comfort movie?” or “What’s a random fun fact about you?” are perfect for casual chat.

5. What if his answers are short or boring?

That might just be nerves—or he’s not that into deep convos. Try asking follow-up questions or share your own answer to keep the flow going. If the energy still feels off, you may not be a match conversationally—and that’s okay too.

6. Are these questions only for romantic interest?

Not at all! You can use them to get to know a guy friend, a new coworker, or even a sibling better. The goal is connection, not just dating.

7. Can I add my own questions to the list?

Of course! Think of this list as your starter pack. You can totally tailor it to fit your personality, his vibe, or the stage of your relationship. Authenticity always wins.

8. What if he asks me the same questions back?

Be ready to answer honestly and openly. These questions are two-way streets—and sharing your side builds trust and keeps the convo balanced.

9. How do I know if he’s giving real answers or just saying what I want to hear?

Pay attention to how he talks, not just what he says. Real answers often come with details, stories, or emotion. If everything sounds too polished, he might be holding back—or just not that comfortable opening up yet.

10. What’s the goal of asking these questions anyway?

The goal is simple: connection. Whether you’re flirting, dating, or deepening a friendship, the right questions help you understand who someone really is—and how they see the world.

Final Thoughts

The truth is, anyone can talk—but real connection comes from curiosity, vulnerability, and shared stories. The 21 questions above aren’t just conversation starters—they’re connection builders.

Whether you’re sitting across from him on a first date, chatting late at night, or even texting from across the world, these questions can help you uncover who he is beneath the surface.

So go ahead—ask, listen, laugh, and maybe even fall a little deeper.

And hey, if you’ve got a favorite question that always sparks an amazing convo, I’d love to hear it. Drop it in the comments below!