Questions to ask your boyfriend: 60 that start a real conversation
The best questions to ask your boyfriend are open, specific and a little unexpected. Ask one at a time, listen to the answer, and answer it yourself afterwards. Below are sixty, sorted from light to deep to flirty, for dinners, long drives and late nights.
How to ask so that he answers
A list of questions fired in a row is an interview. Pick one, ask it when you both have time, and follow where the answer leads. The second question, the one you make up because of what he just said, is the one that matters.
Answer too. A question is an offer to trade, and he will say more if you go second.
Light questions to start with
Good for the first glass, or for a day when nobody wants to be deep.
- What was the best minute of your day?
- What would you eat if it had no consequences?
- Which film have you seen more often than you admit?
- What were you obsessed with at twelve?
- What is your most useless talent?
- Where did you last laugh until it hurt?
- What would you do with a free Tuesday?
- Which smell takes you straight back somewhere?
- What is the worst advice you ever followed?
- What do you order when you want to feel looked after?
- Which job would you try for one week?
- What do you still do exactly like your father?
- What is on your secret playlist?
- Which small luxury would you never give up?
- What did you believe for far too long?
Deep questions to ask your boyfriend
For when the evening is long and the phones are in another room.
- When did you last feel completely yourself?
- What are you proud of that nobody praises you for?
- What did your parents get right?
- What would you do differently if nobody were watching?
- Which friendship do you miss?
- What frightens you about getting older?
- When did you change your mind about something important?
- What do you need when you are sad, and rarely ask for?
- What does a good life look like at seventy?
- What have you forgiven yourself for?
- Where do you feel most at home?
- What would you like to be asked more often?
- Which moment would you live again, unchanged?
- What are you still waiting to be ready for?
- What did the last year teach you?
Questions about the two of you
They work best asked with curiosity, not as a test.
- What did you think when you first saw me?
- When did you know this was something?
- What do I do that makes you feel loved?
- What is your favourite ordinary moment with me?
- What should we do more often?
- What have I taught you without meaning to?
- Where would you take me if we left tomorrow?
- Which of my habits has grown on you?
- What do you want us to be like in ten years?
- What would you like me to ask you for?
- When do you feel closest to me?
- What is a small thing I could do that would mean a lot?
- Which memory of us do you return to?
- What are we really good at together?
- What have you never thanked me for?
Flirty questions for late at night
Ask them slowly. The pause after the question is half of it.
- What were you thinking about me today?
- What is the first thing you notice when I walk in?
- What do I wear that you like too much?
- Where do you most like to be kissed?
- What would you do if I were next to you right now?
- Which moment with me do you replay?
- What should I whisper to you in public?
- What have you wanted to ask me for and have not?
- How would you describe my voice?
- What are you going to do about it?
- What do you want to hear me say?
- What is your favourite way to be woken up?
- Which of us gives in first?
- What would our perfect night look like?
- What are you waiting for?
Try them on someone who always answers
If you would like to hear how a question lands before you ask it at home, try it on Laurent. He is an AI character who answers at length and asks back.
Questions and answers
- What are good questions to ask your boyfriend?
- Open questions that cannot be answered with yes or no, about memories, wishes and the two of you. "What was the best minute of your day?" is a reliable start.
- How many questions should I ask at once?
- One. Let the answer turn into a conversation before you reach for the next.
- What if he gives short answers?
- Answer the question yourself first, in some detail. People match the length and openness they are given.