Questions to Ask Your Boyfriend
These 84 questions to ask your boyfriend give you somewhere to start beyond 'How was work?' Pick a mood, draw a card, and leave room for his side of the story.
A little more about you
Getting to know him
What did you want to be when you grew up?
How to use these questions
- 01
Pick the mood that fits tonight. A silly card can be enough for a tired Tuesday.
- 02
Ask one question, then answer it yourself, too. You can copy or share a card if you're apart.
- 03
Follow the interesting part of his answer. Skip any question that feels too personal or doesn't fit you two.
All 84 questions, by mood
Browse at your own pace. Read one out loud, or print the list for an evening without a screen.
Getting to know him
The routines and little stories you might not hear on a first date.
- What did you want to be when you grew up?
- Which childhood memory always makes you smile?
- Who has had the biggest influence on you?
- What meal could you happily eat every week?
- What's a hobby you'd like me to try with you?
- Which movie do you put on when you need cheering up?
- What were you like in high school?
- What's something you're good at that I haven't seen yet?
- What was your first job like?
- Which family tradition would you like to share with me?
- What could you talk about for hours?
- Where do you go when you want to clear your head?
- What's one thing most people get wrong about you?
- Who would you want me to meet from your childhood?
Fun and silly
A little nonsense for the grocery line or the ride home.
- What would you sing if we did karaoke tonight?
- Which of us would last longer on a camping trip without our phones?
- What embarrassing song do you know every word to?
- Would you rather take a cooking class or a dance class with me?
- What's the funniest thing you've done to impress someone?
- Which TV couple reminds you of us?
- What game are you convinced you could beat me at?
- If we won a vacation tomorrow, where would you take me?
- Which of my habits have you accidentally picked up?
- What was your worst haircut?
- If we entered a talent show together, what would our act be?
- What food do you love that you think I'd refuse to try?
- What's the most ridiculous thing we've laughed about together?
- If we swapped jobs for a day, what would trip me up?
Deep, when you have a little time
One question is plenty. Neither of you owes the other a polished answer.
- What do you need from me after a rough day?
- What's a fear you haven't told me about yet?
- Which dream have you kept to yourself?
- What are you proud of that you rarely talk about?
- When do you feel most understood by me?
- What did your last big mistake teach you?
- What worries you most about getting older?
- Who do you turn to when you need honest advice?
- What's something you wish you'd tried sooner?
- What makes it hard for you to ask for help?
- What do you hope people remember about you?
- What does a happy life look like to you?
- Which belief of yours has changed the most?
- What would you like me to understand better about your past?
Sweet and romantic
For holding hands across the table, even if dinner came in a paper bag.
- What do I do that still gives you butterflies?
- What's your favorite way for me to show affection?
- Where would you take me for a really romantic evening?
- What's a compliment from me that you still remember?
- When do you feel closest to me?
- What's your favorite way to be kissed?
- Which outfit of mine would you pick for our next date?
- What song makes you think about me?
- What's a little thing I do that makes you feel loved?
- When was the last time you wanted to hold my hand?
- What's your favorite thing about cuddling with me?
- What would you say to flirt with me if we met today?
- What's something about me you found attractive before we dated?
- What romantic surprise would you actually enjoy?
Looking ahead
Small plans count, too. You do not have to map out your whole life tonight.
- Where would you love for us to travel together?
- What do you hope we're doing together five years from now?
- What kind of home would you feel happiest in?
- Is having kids something you picture for yourself?
- What does marriage mean to you?
- Which goal would you like my help with this year?
- What should we start saving for together?
- What tradition would you like the two of us to start?
- Would you ever want to live in another country with me?
- How would you like us to spend our next anniversary?
- What adventure would you regret never trying with me?
- What would you like our weekends to look like as we get older?
- How much time with friends would you want in our life together?
- What's one thing you hope never changes about us?
About us, right now
Look at the way you two actually spend your days.
- What was the moment you realized you liked me?
- What did you think of me the day we met?
- What's a memory of us you replay when you miss me?
- What do you remember most about our first date?
- When did you first think we might have a future together?
- What's your favorite photo of the two of us?
- What surprised you about me once we started dating?
- Which date of ours would you love to repeat?
- What do you think we have most in common?
- What's a difference between us that you really like?
- What have you learned about yourself from being with me?
- What's the best meal we've shared?
- Which inside joke of ours still makes you laugh?
- When have you felt especially proud to be my partner?
A few things you might be wondering
What can I ask my boyfriend when conversation feels stuck?
Ask about his childhood, a favorite memory of you two, or something he's looking forward to. Share your answer, too. One question and a little time can be enough to get talking.
Which questions work early in a relationship?
Try Getting to know him or Fun and silly. Save questions about shared routines for when you've had time to build some. You can say, 'We haven't done that yet—what would you pick?'
How do I bring up a deeper question without making it an interview?
Ask whether he has the energy for a longer conversation, then choose just one. Share your own answer and let a pause happen. You can come back to it another day.
Can I send these questions over text?
Yes. Tap Copy to paste one into a message, or Share to use your phone's share menu. Send one at a time so he can answer when he has a moment.
Do these have to be questions for a boyfriend?
No. The prompts address the person you're talking to and work with any partner. Use the name and words you use for each other, and leave out anything that doesn't fit.
Made for a conversation
Written by our team for everyday moments together. These prompts are not a checklist for your relationship. Take what fits and leave the rest.
Curious about your everyday connection?
Our quizzes ask about the way you two spend time, show care and work through things.