These questions are for a guy you’ve just met or are getting to know: a new friend, someone from work or class, or someone you like but aren’t dating yet. They start with easy topics and get more personal further down. If you’re already together, questions to ask your boyfriend fit that stage better, and first date questions cover a first meeting.
Start with something he has mentioned
If he brought up a trip, a job or a game he plays, begin there. A question about something he has already chosen to talk about is easier to answer than one pulled from a list, and it shows you were listening.
Let him ask you too
Answer your own questions when it fits, at about the same depth as his answers. Notice whether he asks anything back. You’ll learn as much from that as from any single answer.
Save the last group for later
The deeper questions ask about fears, hard periods and what he finds hard to forgive. Wait until he has shared something personal on his own, and don’t press if he keeps it short. A friendly conversation about values doesn’t mean he’s interested in dating, and a guarded answer doesn’t mean he isn’t. If you want to know, ask that directly.
For more ways in, see getting to know you questions or our interview guide.