Questions to ask your boyfriend
The first months with someone are mostly guessing. These 40 questions to ask your boyfriend are for that stretch: you like him, and you're still finding out who he is. What comes after each question matters more than the question: in first conversations, people who asked more follow-up questions were liked more,1 and pairs who took turns sharing liked each other more than pairs who talked in long stretches.2
How to use these. Ask one, then ask about his answer before moving on. Answer it yourself too. Skip anything that feels like an interview. Three good questions on a long walk beat twenty over dinner.
Nothing here assumes how men talk or what they want. These work for anyone you've started dating. There are no "test his love" or "trap" questions. A question you've already decided the right answer to isn't a question.
Easy openers for a slow evening
Low stakes. Quick to answer. Often the start of a much longer story than the question deserves.
Which place you've lived do you miss most, and what do you miss about it?
Answer this with JoyWhere he comes from
His family and hometown explain a lot of habits you'll notice later. Ask with curiosity, and let him decide how much to share.
Tell me about a time a teacher or coach changed how you saw yourself.
Answer this with JoyWhat he cares about
Work, hobbies, and the things he'd defend in an argument at a party. Pride lives here.
His people
Listen to how he talks about his friends. Fondly? Like rivals? Not at all?
Which friend has known you the longest, and what would they tell me about you?
Answer this with JoyTell me about a time a friend showed up for you when you didn't expect it.
Answer this with JoyWhy the follow-up matters more than the question
A team at Harvard studied live get-to-know-you chats and speed dates, and found that people who asked more questions, especially follow-ups, were liked more by the person they talked to.1 The speed dates went further. Daters who asked more follow-ups were more likely to get a yes for a second date.1 Here's the twist. People in the studies didn't expect asking questions to make them more liked.1
A follow-up picks up something from the answer. Here is one opener and three follow-ups. The example is written for this page.
- Opener: What's something you were obsessed with at twelve?
- His answer: Skateboarding. I was at the park every day.
- Follow-up: What got you to the park every day?
- Follow-up: Do you still have the board, or did something end it?
- Follow-up: What did skating give you that school didn't?
Going deeper, in turns
Pairs of strangers who spent 45 minutes on sharing tasks that slowly got more personal felt closer afterward than pairs who made small talk, in a 1997 study by the psychologist Arthur Aron's team.3 Turns matter too.2 Pairs who swapped back and forth liked each other more than pairs where one person talked for a long stretch, then the other.2
Ask these one at a time, and answer each one yourself, before he does or right after, so the talk goes back and forth instead of becoming two speeches.2
"You asked what I'm afraid people will find out. Honestly? That I'm not as confident as I look at work. Your turn. Same question."
The example was made up for this page.
What's a memory from childhood you think about more than you'd expect?
Answer this with JoyTell me about a time you changed your mind about something important.
Answer this with JoyWhere this is going
At some point you'll want to know what you are. These are kinder than "So, what are we?" and easier to answer honestly. If you're months in and still can't tell, situationship covers that.
How do you like to handle it when something bothers you about someone you're dating?
Answer this with JoyWhat would you want to know about me before you'd call me your girlfriend or partner?
Answer this with JoyTell me about a time a past relationship taught you something you still use.
Answer this with JoyFor a text conversation
For the days apart. Short to read, easy to answer from a bus seat or a break room.
Send me a photo of something you can see right now, and tell me why you picked it.
Answer this with JoyQuestions people ask
What are 21 questions to ask your boyfriend?
"21 questions" is a back-and-forth game where you each take a turn asking. For the early months, try this set. Take the six easy openers and the six "where he comes from" questions. Add five from "what he cares about" and four from "going deeper". Take turns, which is what the research suggests helps.2
What are 10 deep questions to ask your boyfriend?
Start with the six in "Going deeper, in turns". Then add four from elsewhere on the page:
- Who in your family are you most like?
- What's a goal you've had for years and haven't started yet?
- What's an opinion you hold that most of your friends don't share?
- What's on your mind tonight that you haven't said to anyone?
Deep questions work best after easier ones, the way Aron's study built up slowly.3
Are there questions to test his love?
Not honest ones. A question built to catch him out tells you how he handles a trap. It can't tell you how he feels. If something specific worries you, ask about that directly. If worry keeps taking over, trust issues may help more than any question.
What if he gives one-word answers?
Ask one follow-up about the one word ("Skateboarding? Since when?"). Try asking side by side, on a walk or in the car, instead of across a table. Give it time. If it's always one word, that's worth noticing too.
More questions and guides
- Questions to ask your partner, for couples who've been together a while.
- Questions to ask your girlfriend, for going past small talk.
- Love languages, for finding out what makes him feel cared for.