Questions to ask your boyfriend
39 questions for the boyfriend you already know the basics about — built for a bored Tuesday, a long text thread, and the specific pleasure of asking something he has to think about before answering.
Easy ones, to start
Nobody opens with the hard question. These are the ones you can ask with the plates still on the table, and they still tell you something.
- Who in your life gets less credit than they deserve, and what do they actually do?
- What kind of day makes you want people around, and what kind makes you want to disappear for an hour?
- What do you notice first when you walk into a room full of people you don't know?
- What's your most reliable excuse for getting out of something?
- What are you like on the phone to people who aren't me?
- What's a completely ordinary part of your life I've never actually seen?
- What are you like when you're the one who has to pick where we eat?
- What's the most fun you've had recently doing something that sounds boring described out loud?
- Which of us says the thing out loud, and which one was already thinking it?
- What's the pettiest reason you've ever gone off someone?
- What are you bad at and have absolutely no intention of getting better at?
Questions that actually go somewhere
The middle rung. Still safe, but the answer is about who someone is rather than what they did, which is the whole difference.
- On a bad day, do you want me to ask what's wrong or leave it — and have you ever actually decided?
- What do you do with a feeling you'd rather not be having?
- What do you think you're like to be in a relationship with? Not the good version — the accurate one.
- What's the thing you do to get people to like you that you can catch yourself doing?
- What have you been told about yourself so often that you stopped checking whether it's true?
- What are you getting wrong at the moment, in any part of your life?
- What kind of pressure are you under right now that you'd never call pressure?
- What's the last thing you wanted badly and then talked yourself out of wanting?
- What have you decided about yourself that you're not sure is actually true?
- What's a decision you made mostly to prove something to somebody?
- Who do you go to first when something's gone wrong, and where do I come in that order at the moment?
- Which of your friendships is doing most of the work at the moment, you or them?
- What's the version of yourself you put in front of an interviewer, and how much of it do you believe?
The ones most people never get to
Ask these when there is time and nobody has to be anywhere.
- Where do the person you think you are and the person you actually are stop lining up?
- What do you think you owe the people who got you this far, and are you paying it?
- What's true about you that you've never managed to say out loud in a way that came out right?
- What have you needed from me that you'd find it hard to admit you needed?
- What are you most afraid I'll eventually get tired of?
- What's still on hold in you, waiting to see how this goes?
- Who would you have to stop being to be all in with somebody?
- What's the part of you that usually turns up about six months in that I haven't met yet?
When something is off
The ones people skip. Skipping them is usually why the same thing keeps coming back.
- What's something about your life you've been giving me the short version of?
- What's the first thing you do when you can tell a conversation is about to be difficult?
- Who have you hurt in a way you'd handle completely differently now?
Where things are going
Fewer of these on purpose. A conversation that is only about the future is a planning meeting.
- What do you want to get good at purely for your own sake?
- What have you stopped competing at, and was that a decision or did it just go quiet?
- What are you working towards that you'd be embarrassed to have to explain out loud?
- Who were you two years ago that you're relieved not to be now?
Some questions are easier to answer when neither of you chose them.
That’s why we made them into a wheel. Spin it — this one is loaded with the questions on this page.
Press spin. You do not get to pick.
Does any of this actually work?
A large share of the demand for this page is for questions to test him, and that is the one design that reliably returns nothing. The relevant evidence is about who gets rewarded for candour and when. Among 176 married and dating couples, dating people were most intimate with partners who evaluated them favourably, while married people were most intimate with partners whose view matched their own self-view. Earlier in a relationship, the honest answer is the riskier one to give. A question that is visibly scored invites the answer that scores, and you learn what he thinks passes.
He is also judging his own honesty more harshly than you are. Seven studies found a consistent gap between how people rate their own vulnerability and how they rate the same act in someone else — admitting a mistake, asking for help, saying how they actually feel. From the inside it looks like weakness; from the outside, watching, it looks like courage. The proposed mechanism is that you construe your own exposure concretely, so the downsides dominate, and someone else’s abstractly, so the upsides do.
The mechanically useful part is unglamorous. When one person in each of 199 chatting pairs was told privately to ask at least nine questions and the other at most four, the high askers were better liked — and what carried it was follow-up questions, which is what listening actually looks like from outside. The askers did not expect it to work. The second question does more than a better first one.
Swann, De La Ronde & Hixon (1994), Authenticity and positivity strivings in marriage and courtship, Journal of Personality and Social Psychology · source
Bruk, Scholl & Bless (2018), Beautiful mess effect: Self–other differences in evaluation of showing vulnerability, Journal of Personality and Social Psychology · source
Huang, Yeomans, Brooks, Minson & Gino (2017), It doesn’t hurt to ask: Question-asking increases liking, Journal of Personality and Social Psychology · source
He does not have to answer all of them and a question he dodges is still an answer. If this reads to him as a test — and "questions to test his love" is what a lot of people are actually searching — he will perform the answer he thinks passes, which is the one outcome that tells you nothing.
Last checked 28 August 2026.