10 Interesting Things to Talk About With a Boy

Let’s face it—talking to a boy, whether you just met or you’ve known him for a while, can sometimes feel like walking a tightrope between too boring and too intense. But here’s the good news:

You don’t need to overthink it.
You just need to spark his interest.

The best conversations happen when you stop trying to impress and just try to connect. And to do that, you’ll need some interesting things to talk about with a boy that go beyond the usual “what do you do for fun?”

• You can check the list of interesting topics to talk about with a girl

So, whether it’s a new crush, your guy best friend, or your boyfriend—you’ll love this list of 10 interesting conversation topics that keep things fun, thoughtful, and even flirty (when needed).

1. His Biggest Childhood Dream

Ask: “When you were little, what did you want to be when you grew up?”
This question taps into his past while also revealing how he’s changed. You’ll learn about his early passions, wild imaginations, and maybe even the moment he gave them up.

2. The Craziest Thing He’s Ever Done

Boys love a chance to share their “wild stories.” Whether it’s something spontaneous, adventurous, or just plain ridiculous—it’s bound to be a fun moment.

You might say, “Okay, tell me the most insane thing you’ve ever done that you actually don’t regret.”

3. His Take on Love and Relationships

This is where things get deeper. Try asking: “What’s something you think people misunderstand about love?”

You’ll be surprised how open some guys get when asked the right way. Keep it casual and let him take the lead—some boys love opening up when they feel it’s safe.

4. His Dream Life (If Money Wasn’t an Issue)

Ask him: “If you had unlimited money and zero responsibilities, what would your life look like?”
Would he live in a mansion or a camper van? Would he run a business or chill on a beach forever? This gives you insight into his values and imagination.

5. Video Games, Movies, or Shows He’s Obsessed With

This might sound basic—but trust me—it’s where a lot of guys feel most comfortable.
Let him nerd out a little. Ask him to recommend a game or a series. You’ll not only see what excites him, but you might also find common ground.

Bonus: If you ask him to explain a game or storyline to you, he’ll secretly love that you’re interested.

6. His Opinion on “What Makes a Man?”

Ask: “Do you think society puts pressure on men to act a certain way?”
It sounds deep—and it is—but guys often don’t get asked things like this. And once they start opening up, the conversation gets very real, very fast.

7. His Worst and Best Date Stories

This one’s fun and revealing. You’ll get some laughs, maybe some what-not-to-do moments, and you’ll also understand what kind of vibe he enjoys when dating someone.

You can say, “Be honest—what was your most awkward date ever?” Then, share yours. It sets a light tone.

8. What He Thinks About Friendship

Friendships mean a lot to guys, even if they don’t talk about it often. Ask: “What do you value most in a friend?”
Or try, “Who’s your ride-or-die, and how did you meet?” It’s a meaningful topic that shows him you care about what matters to him.

9. Would You Rather… (But Make It Clever)

Switch up the usual “Would You Rather” game with fun but unique questions:

• Would you rather lose all your money or all your memories?
• Would you rather fight a lion once or argue with your ex every day for a month?
• Would you rather time travel to the past or the future?

These random yet interesting prompts create hilarious and thoughtful debates.

10. What Motivates Him When No One’s Watching

Ask: “What keeps you going on days you feel like giving up?”
This reveals what he’s made of—his internal drive, his sense of purpose, or even his personal struggles. It’s one of those topics that can shift a casual talk into a genuine connection.

Make Him Feel Heard

When you’re searching for interesting things to talk about with a boy, remember—it’s not just what you say, it’s how you ask.

Make your questions thoughtful, not interrogative. Keep the vibe light, but don’t be afraid to go deep if the moment feels right.

Real connection doesn’t come from perfect words—it comes from curiosity and presence.

The more you show interest in what makes him him, the more he’ll open up.

So whether it’s his childhood, his fears, his passions, or his favorite movies—make it a moment he won’t forget.