Questions to Ask a Guy: 45 Ideas to Know Him Better

What are good questions to ask a guy?

Good questions ask for a story or a preference. "What's the best thing you've eaten this month?" gives him room to answer and gives you something to follow up on. Choose the stage that fits, ask one or two questions, and then answer one yourself.

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Questions for a guy you just met

At the start, keep it light and low pressure. You are just having a good conversation.

1. What's the best thing you've done this week?
2. What do you do when you have a free Saturday?
3. How did you end up in this city?
4. What's your go-to order at a coffee shop or bar?
5. What's a show or movie you recommend?
6. What's your favorite thing about your job, and what's the worst?
7. Are you a morning or a night person?
8. What's the best trip you've taken?
9. What's a skill you picked up on your own?
10. What do you do to unwind after a long day?

Questions to ask a guy over text

Text strips out tone, so short and specific questions work best. Skip anything that needs a long answer typed on a phone.

11. What are you up to this weekend?
12. What's the best song you've heard lately?
13. What was the high point of your day?
14. Quick one: pizza or tacos?
15. What are you watching right now?
16. What's the app you use most?
17. What's a place near you that you'd recommend?
18. What's a food you'd defend to the end?
19. What would you do with a day off tomorrow?
20. Tell me about something you're looking forward to.

Questions for getting closer

When you have met a few times, move toward what he cares about and how he lives.

21. Who's a person who influenced you most?
22. What's something you worked hard for?
23. What was your family like growing up?
24. What are you building toward in the next year?
25. What do you like about your friends?
26. How do you spend a day when you're stressed?
27. What would make a great date for you?
28. What's something you've changed your mind about?
29. What's a hobby you'd love to share with someone?
30. What's something you're proud of that most people don't know?

Deeper questions

These show whether you want the same things from life, so keep them for a calm moment once you trust each other. Answer them yourself, too.

31. What do you want your life to look like in five years?
32. What matters most to you in a relationship?
33. How do you like to be supported when things are hard?
34. What would you never compromise on?
35. How do you feel about money: saving, spending or sharing?
36. How do you want family to be part of your life?
37. What do you want to be known for?
38. What's something you're still figuring out?
39. What's a fear you can talk about?
40. What does a good partnership look like to you?

Playful questions

Use these when the mood is relaxed.

41. What superpower would you pick, and what would you actually use it for?
42. What's the most random thing you're good at?
43. What would you do if you won a small lottery?
44. What's your most overrated thing and your most underrated?
45. If you opened a restaurant, what would be on the menu?

For longer lists that work at any stage, see our page of deep conversation questions. For a general list that fits anyone, see questions to get to know someone, and for a first meeting see first date ideas.

How to read his answers

Treat his answers as information about what he is like.

Notice how he answers. Does he ask you something back? Does he stay engaged when you talk? A good conversation goes both ways.

Ask a follow-up. In a 2017 study in the Journal of Personality and Social Psychology, people who asked more questions, especially follow-ups, were liked more by their conversation partner.

Don't over-read one answer. A short reply may mean he was busy or nervous, not that he isn't interested. Look for patterns over several conversations.

Match the pace. You feel closer to someone when you both share, not just one of you. In one experiment by Arthur Aron and colleagues, strangers who worked through tasks that grew gradually more personal felt closer afterward than strangers who did small-talk tasks.

When to stop asking

If he keeps changing the subject or gives one-word answers, ease off and try again another day. If something he says makes you feel uncomfortable, trust that feeling. When you meet someone from the internet, our trust and safety page has practical steps, and the National Domestic Violence Hotline is free and confidential at 1-800-799-7233. In an emergency call 911.

Summary

Start light, ask about his real life, follow up and share your own answers. Pay attention to whether you feel relaxed talking to him. If it is a crush you are talking to, questions to ask your crush is a better fit. For more ideas, browse Jastado Stories and our page of deep conversation questions.