Questions to Ask a Guy That He’ll Actually Enjoy Answering

The best questions to ask a guy are about something he already cares about: what he’s doing, what he’s proud of, what he’d pick. Ask one, follow his answer, and share something of yours before the next question.

30 good questions to ask a guy (and what to skip)

When you first meet 6
Light and fun 5
Getting to know him 8
Texting and early dates 3
Going deeper 8

You're on a fifth date with Ezra at a quiet wine bar. It's going well, and you'd like to know how he thinks about love without asking something heavy like 'why did your last relationship end?' A minute ago he pulled up photos from his grandparents' 60th anniversary party last weekend.

Ezra

is holding his phone out to you, zoomed in on a photo of his grandparents slow-dancing, grinning and shaking his head a little

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30 good questions to ask a guy (and what to skip)

These questions to ask a guy run from easy and funny to more personal. Each row says when to ask, what to ask, and the version that tends to fall flat.

When you first meet

He just finished setting something up“Okay, you’ve earned a veto. What are we watching tonight?”Skip: “Nice job.” (and nothing else)
At a party where you both know the host“How do you know Sam? I want the unofficial version.”Skip: “So what do you do?” as your first line
He orders without looking at the menu“Okay, regular. What should I get here?”Skip: “Do you come here a lot?”
He just got back from a trip“What’s one thing from that trip you’re still thinking about?”Skip: “Was it fun?”
He’s wearing a team jersey“How long have you been suffering with this team?”Skip: Pretending to love a team you’ve never watched
He brings up his dog“What’s the dumbest thing your dog does that you secretly love?”Skip: “What breed?” and then moving on

Light and fun

The conversation needs a lighter turn“What’s a hill you’re willing to die on that nobody else cares about?”Skip: “Tell me a fun fact about yourself.”
You’re talking about food“What’s the most overrated food that everyone pretends to like?”Skip: “What’s your favorite food?”
He says he’s competitive“What’s the pettiest thing you’ve ever been proud of winning?”Skip: “So are you a sore loser?”
Things are relaxed and silly“If you had to be famous for one useless talent, what would it be?”Skip: Hypotheticals that are really tests, like “would you ever cheat?”
He’s telling a funny story“Wait, what happened next? Don’t skip the good part.”Skip: Topping it with your own story right away

Getting to know him

You want to hear about him as a kid“What were you weirdly good at when you were ten?”Skip: “What were you like in high school?”
You want more than his job title“What part of your job would you do even if nobody paid you?”Skip: “Do you like your job?”
He mentions a free weekend“If you had a whole Saturday with no plans, what would you do?”Skip: “What are your hobbies?”
He talks about where he grew up“What’s something people get wrong about your hometown?”Skip: “Would you ever move back?” right away
He mentions the same friend a few times“How did you and Marcus become friends?”Skip: Forgetting the name he’s said three times
He mentions a brother or sister“Are you two alike, or total opposites?”Skip: “Are you close with your family?” (too broad)
He’s reading or watching something“What made you pick that up?”Skip: Reviewing it for him before he answers
He’s learning something new“What’s been the hardest part so far?”Skip: “Why would you want to learn that?”

Texting and early dates

You’ve been texting and it’s all “wyd”“What was the best part of your day, even if it was small?”Skip: “wyd” for the fourth night in a row
Second or third date“What’s something you’re looking forward to this month?”Skip: “So what are you looking for?” in the first ten minutes
He remembered a small thing you said“You remembered that? Okay, your turn. What should I know about you?”Skip: Brushing it off with “it’s nothing”

Going deeper

You want to know what he values“Who’s someone you really admire, and why?”Skip: “What’s your biggest weakness?”
He shows you photos of a couple he admires“What do you think they figured out that most people never do?”Skip: “So why did your last relationship end?”
He mentions his kid, then apologizes“You don’t have to apologize. You smiled at that. What’s she like?”Skip: “No worries!” and a quick new topic
A quiet moment after a good date“What’s something you’ve changed your mind about in the last few years?”Skip: “Where do you see yourself in five years?”
Talking about love, lightly“What’s the most romantic thing you’ve ever seen someone do? Doesn’t have to be you.”Skip: “How many people have you dated?”
He opens up about a hard year“What got you through it?”Skip: Jumping in with advice
You’ve been seeing each other a few months“What’s one thing you wish more people asked you about?”Skip: “Do you ever think about us?” as a test
He answers a big question honestly“Thanks for telling me that. Can I tell you mine?”Skip: Rushing to the next question on your list

Personal questions to ask a guy, and when to ask them

Deeper questions to ask a guy land best once he’s already shared something on his own. A good sign is when his answers get longer and he starts asking you things back. Then ask about what matters to him: a person he admires, a choice he’s proud of, what he’s learned about love from people around him. If a question lands flat, don’t push. Go back to something easy and try a deeper one another day.

How to use these questions to ask a guy

A list of questions to ask a guy is only half the job. The other half is asking at the right moment and doing something with his answer.

1 of 4

Tie the question to what’s in front of you

The easiest questions to ask a guy are about something happening right now: the game on the bar TV, the project he just finished, the photo he’s showing you. “What should I order here?” is easier to answer than “what are your hobbies?”

Your date, at a barbecue place

Okay, fair warning, I have strong opinions about brisket.

Flat reply

“Ha. So what are your hobbies?”

“Uh… hiking, I guess?” The brisket opinions stay locked up.

Better reply

“Strong how? Is this place getting it right or not?”

He leans over the tray: “Okay, so the bark is good, but…”

Why it works: A question about what’s in front of you is easier to answer than “hobbies.”

2 of 4

Ask what he’d pick, not who he is

Choice questions like “what would you watch if nobody could argue?” let him show his taste and defend it a little. They’re fun questions to ask a guy you just met because there’s no wrong answer.

A friend of a friend, on a road trip

I’m good with whatever music.

Flat reply

“Cool. So what kind of music are you into?”

He shrugs: “Uh… a little of everything?”

Better reply

“Nope. You get one song. Pick it and defend it.”

He thinks for a second, then grins: “Okay. Don’t laugh.”

Why it works: Asking what he’d pick is easy to answer and shows his taste.

3 of 4

Follow his answer before asking the next thing

The follow-up is where you actually get to know him. If he says he’d spend a free Saturday fishing, ask where, or who taught him. One good follow-up beats three new questions — that’s true of most dating tips.

Your date, on a first date

Most weekends I’m in the garage, fixing up my grandpa’s old tools.

Flat reply

“Nice. What other hobbies do you have?”

He lists a couple more, and it stays on the surface.

Better reply

“Wait, his actual tools? What are you working on right now?”

He pulls out his phone: “Okay, so this is a hand plane from the fifties.”

Why it works: Follow his answer. One good follow-up beats three new questions.

4 of 4

Trade answers, then go a step deeper

Answer your own questions too. Once you’ve both shared something, you can move to more personal questions to ask a guy: who he admires, what he’s working toward, how he thinks about love. If his answers get short, go back to lighter ground, or to easy first date questions.

A guy you’ve been seeing for a month

Mine’s probably my dad. He opened his own shop at fifty. What about you?

Flat reply

“Oh, I don’t know. So did the shop work out?”

He answers, but it starts to feel like you’re interviewing him.

Better reply

“My aunt. She went back to school at forty. Sounds like your dad didn’t wait for a perfect time either.”

He nods slowly: “Yeah. I think about that a lot, actually.”

Why it works: You traded an answer of your own, so going deeper feels fair, not nosy.

Questions to ask a guy: common mistakes

Running a checklist. Ten questions in a row feels like a screening, not a date.
Opening with his exes or why he’s single. Those are later stories.
Asking “juicy” questions to test him. Questions meant to catch someone out get a guarded answer.
Not answering back. If he asks the same question in return, have a real answer ready.

Questions to ask a guy: FAQ

What are good questions to ask a guy?

Good questions to ask a guy are specific and easy to answer: what he’d pick, what he’s proud of, what he’s into right now. “What would you do with a free Saturday?” works better than “what are your hobbies?” because he can picture the answer. Then follow what he says.

What are fun questions to ask a guy you just met?

Fun questions to ask a guy you just met are about the moment you’re in: how he knows the host, what he’d order, what he thinks of the music. Light choice questions work too, like “what’s the most overrated food?” Save personal questions until you’ve talked for a while.

What questions do guys love to be asked?

Most people, guys included, enjoy questions about something they know well or care about: a skill, a team, a project, a trip, their dog. Asking for his take on something (“what would you check first?”) often works better than asking him to describe himself.

What are questions to ask a guy about love?

The easiest way in is through someone else’s relationship: “What do you think your grandparents figured out?” or “What’s the most romantic thing you’ve seen someone do?” They tell you how he thinks about love without asking about his exes.

What are personal questions to ask a guy you like?

Personal questions to ask a guy you like include who he admires, what he’s changed his mind about, and what he’s looking forward to. Ask them once you’ve both shared a bit, and answer them yourself too, so it feels like a trade and not a test.

Meet Communicate Better

A list of questions is easy to read. Asking the right one in the moment takes practice.

Communicate Better is built for one thing: helping you communicate better. Step into real moments, say it your way, and see how it lands — until the right words come without thinking.

Learn more about Communicate Better →

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