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Questions to ask your boyfriend: 128 of them, sorted by how long you have been together

The best questions to ask your boyfriend are the specific ones: a memory, a plan, a bad Tuesday. Below are 128 in eight groups, from cute to deep, plus a random picker that draws one at a time and keeps the ones you choose.

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Free picker · copy or print your listNo sign-upAbout 9 min read
Questions to ask your boyfriend over a late snack: two mugs, a bowl of nuts, blank cue cards and a phone with the Alpacto home screen on a kitchen counter

One question on the screen, two people answering it.

In short

Open the picker, choose the group that fits how long you have been together, and draw a question. Keep the ones you like, skip the rest, and ask one follow-up about his answer before you draw the next.

Five to nine questions make a good evening. Start with the cute and funny groups, then move toward deep and future as the evening goes on.

Random questions to ask your boyfriend: draw one, keep the good ones

Pick a group, or leave it on all groups for a random mix. Keep adds a question to your list, and Skip hides it for the rest of your visit. The list stays in this browser and goes nowhere else.

Questions I want to ask my boyfriend

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Press Next question to draw one.

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Nothing kept yet. Press Keep on a question you want to ask.

    Which questions to ask your boyfriend at each stage

    The same question can be sweet in month two and abrupt in week two. Use these four cards to choose where to start.

    Early dating, the first three months

    You are learning what he is like on an ordinary day. Draw from Cute, Funny and The past, two or three at a time, and leave Deep for an evening that already feels slow.

    Getting serious, three months to a year

    This is when serious questions to ask your boyfriend start to fit: how he handles stress, what he wants from the next year. Add Deep and About us, and ask on a drive or over dinner prep.

    Living together, or about to

    You are about to share a bathroom and a budget. Go through Before moving in first, then The future, on a weekend morning and not at midnight.

    Together for years

    You know his answers from five years ago, so ask about now. Deep and The future show what changed, and the Cute group is worth repeating.

    How to ask your boyfriend a question so he gives a real answer

    Ask while your hands are busy. Driving, cooking, walking the dog and folding laundry take the pressure off both of you, and a short silence feels natural instead of awkward.

    Make the question specific. Do you ever feel stressed at work? gets a shrug. What was the worst ten minutes of your Tuesday? gets a story.

    Answer first, then follow up

    Answer your own question before he does, at the length you hope to hear back. Then ask one follow-up about what he says. If he says work was fine, try fine good, or fine nothing happened?

    Research on follow-ups: in a 2017 paper on live conversations, people who asked more questions, and follow-up questions in particular, were better liked by the person answering. The same authors found that people do not expect this effect before they try it. Source: Huang et al., Journal of Personality and Social Psychology, 2017.

    Let him pass

    Any question can be passed without a reason. A passed question goes back in the pile, which is what the Skip button does on screen. The one he skips in March may be the one he picks up in June.

    128 questions to ask your boyfriend, in eight groups

    The groups run from light to heavy, and the numbers let you say let’s do 49 to 56 tonight and stop there. Every question is written to him, and none repeats the 120 on our questions to ask your partner page, which has six rules for asking and a printable deck.

    Cute questions to ask your boyfriend

    Sixteen that are meant to make him smile before they make him think.

    1. What is the first thing you noticed about me that you did not say out loud?
    2. Which text from me have you reread more than once?
    3. What nickname for me would you never use in front of your friends?
    4. What did you tell your family about me the first time?
    5. Which song do you now think of as ours, even though we never picked one?
    6. Where in this city do you want to take me that you have not yet?
    7. What small thing do I do in the morning that you secretly like?
    8. Which outfit of mine do you remember better than I do?
    9. When did you first catch yourself smiling at your phone because of me?
    10. What would you cook for me if you had to impress me from scratch tomorrow?
    11. What is a compliment you have saved up and not given me yet?
    12. Which of my laughs is your favorite?
    13. What do you think my face looks like when I am concentrating?
    14. What do you do on the days when you miss me?
    15. If you could send me one surprise at work, what would it be?
    16. Which friend of yours gets the most details about us, and what do they hear?

    Funny questions to ask your boyfriend

    Sixteen for the car, the couch, or a bad mood that needs breaking.

    1. What is the dumbest argument you have ever won?
    2. What would be your wrestling entrance song, and what would they call you?
    3. Which lie did you believe for far too long as a kid?
    4. What is the most embarrassing playlist you have ever made?
    5. If this week were a sitcom episode, what would it be called?
    6. Which of your friends is secretly the worst driver?
    7. What do you do alone in the car that you would never do with me in it?
    8. If you woke up as me for a day, what would you do first?
    9. Which animal would beat you in a fight, and which would you beat?
    10. What is your emergency excuse for leaving any party early?
    11. What is the weirdest rule at your family’s dinner table?
    12. Which childhood nickname do you wish you could erase?
    13. If you had a late-night infomercial, what would you be selling?
    14. What is the silliest thing you have ever been competitive about?
    15. Pineapple on pizza: take a side and defend it for one minute.
    16. If your fridge could talk, what would it tell me about you?

    Questions about his past

    Sixteen about the years before you, which are the ones he has told the fewest times.

    1. What was the best summer of your life, and who was in it?
    2. Which teacher or coach changed how you see yourself?
    3. What is the story your friends tell about you that is actually true?
    4. Who was your first crush, and what did you do about it?
    5. What did you do on the day you got your driver’s license?
    6. What was the lowest point of your twenties, and what got you through it?
    7. Which move or change of school was hardest for you?
    8. What toy or game did you play until it broke?
    9. What did you eat in the first place you lived on your own?
    10. Which old friend do you think about most often?
    11. What was the first concert or game you went to, and who took you?
    12. What did you get in trouble for as a teenager?
    13. What is the best advice a grandparent or an older relative ever gave you?
    14. What did you learn from your last relationship that you do differently now?
    15. Which photo from your childhood tells me the most about you?
    16. What was the soundtrack of your high school years?

    Deep questions to ask your boyfriend (the serious ones)

    Sixteen for a slow evening, with no phone and no plans afterward.

    1. What part of growing up do you only talk about late at night?
    2. When did you last feel like you were pretending, and who was it for?
    3. What do you need to hear when you have failed at something?
    4. What does being a good man mean to you, and where did you learn it?
    5. What are you still working through that I have not asked about?
    6. Which of your friendships has changed the most in the last few years, and why?
    7. What do you wish somebody had told you at eighteen?
    8. What would you want your family to say about you at your eightieth birthday?
    9. What do you lose sleep over that sounds small when you say it out loud?
    10. When is it hardest for you to ask me for help?
    11. What is the hardest conversation you have ever had to start?
    12. What did you give up that you still miss?
    13. When do you feel the most pressure, and who puts it there?
    14. What do you do to look fine when you are not?
    15. Which belief of yours do you hold only because you were raised with it?
    16. What kind of support from me would feel like support and not like fixing?

    Questions about us

    Sixteen that stay inside the relationship and ask what he actually thinks of it.

    1. Which moment in our relationship do you replay the most?
    2. What do we do well as a team that you want to keep doing?
    3. When did you feel that I understood you best?
    4. What do I do that makes an argument end faster?
    5. What do you wish we did more often?
    6. What was your first impression of me, and how wrong was it?
    7. Which of our fights taught you the most?
    8. What do you think our friends say about us when we leave the room?
    9. How can you tell I am upset before I say anything?
    10. What do I do that makes you feel trusted?
    11. What should we do differently in a week when we are both busy?
    12. What is the best surprise we have had together?
    13. Are you happy with how we split time between friends and each other?
    14. How do you want to celebrate small wins together?
    15. What is a question about us that you have wanted to ask for a while?
    16. How many evenings a week together is ideal for you, and what do they look like?

    Questions about the future

    Sixteen that tend to turn into plans, so keep a pen nearby.

    1. What would a good year look like for you, from January to December?
    2. What job would you take if the pay were the same everywhere?
    3. Which city have you thought about living in more than you let on?
    4. What is one thing you want us to try before the end of next summer?
    5. What kind of home do you picture, down to the front door?
    6. How do you imagine holidays when we are older: whose house, which food?
    7. What would you want to teach a kid in your life that nobody taught you?
    8. What does a retirement morning look like to you?
    9. How much of the future do you plan, and how much do you leave to luck?
    10. What would make you say yes to moving for a job, and what would make you say no?
    11. What do you want to be much better at ten years from now?
    12. What big purchase are you quietly saving for?
    13. What worry about the next five years would you like to talk through together?
    14. Which tradition from your family do you want to carry into ours?
    15. If we took a year off together, what would we do with it?
    16. What would tell you that we are on the same page about money?

    Questions to ask your boyfriend before moving in together

    Sixteen practical ones, best asked on a weekend morning rather than at midnight.

    1. Walk me through a regular weeknight: who cooks, who does the dishes, and when?
    2. How do you feel about sharing a closet, a bathroom, and a bed on bad nights?
    3. What time do you go to sleep and wake up when nobody is watching?
    4. How tidy is tidy to you, and what kind of mess can you not stand?
    5. How should we split rent and bills: evenly, by income, or some other way?
    6. Which of your things are non-negotiable to bring?
    7. How many nights a week do you want the place to ourselves?
    8. How do you feel about guests staying over, and for how long?
    9. Which chores do you actually like, and which do you avoid?
    10. What does a quiet evening at home look like for you?
    11. What is our plan if one of us loses a job or has a gap in income?
    12. How do we handle the thermostat, the TV, and the noise?
    13. Do you want a pet, and who would take care of it day to day?
    14. How should we handle the first big argument in the new place?
    15. What is a rule from your family’s home that you would bring along?
    16. How do you tell me that you need to be alone in the home, and how should I take it?

    Flirty questions to ask your boyfriend (spicy, but clean)

    Sixteen that flirt without going anywhere you would not read aloud at brunch.

    1. What do you remember about our first kiss?
    2. Where have you most wanted to kiss me?
    3. When did you last see me across a room and think, wow?
    4. What do I wear that you like most?
    5. What would you plan for a date if the only goal was to make me blush?
    6. What is the most romantic thing you have done, and would you do it again?
    7. What is a flirty text you have wanted to send me and did not?
    8. When am I most attractive to you in a way that has nothing to do with looks?
    9. Where would you take me for a weekend with no plans?
    10. Which song would you pick for a slow dance in our kitchen?
    11. What is hard to say out loud about how you feel when we are close?
    12. What do I do that still gives you butterflies?
    13. What would a perfect lazy morning with me involve?
    14. Which memory of us makes you grin when it comes back?
    15. How do you like to be flirted with in public?
    16. If we had one night in a hotel with no phones, what would we do first?
    Eight groups, numbered straight through. Pick one and stop there.

    What to do with his answers

    Some answers are plans: a weekend away he has never mentioned, a skill he wants you to learn together. Write those down while he is still talking.

    If you want a game instead of a list, try would you rather questions for couples, or print the 48 cards of the couple questions game. If a wedding is on the horizon, Questions to ask before marriage picks up where the moving-in group stops.

    Questions people ask

    What are 21 questions to ask your boyfriend?

    Take three from each of the first seven groups: questions 1 to 3, 17 to 19, 33 to 35, 49 to 51, 65 to 67, 81 to 83 and 97 to 99. That gives you 21 that run from cute to practical. Swap in the flirty group for any of them if you want the evening lighter.

    What are 50 juicy questions to ask a boyfriend?

    Juicy means personal and a little flirty. Use the whole Deep group (49 to 64), the whole About us group (65 to 80) and the whole Flirty group (113 to 128). That is 48, and the last two are yours to write.

    What are 20 flirty questions to ask him?

    Questions 113 to 128 are the flirty group, 16 in all. Add the first four cute questions, 1 to 4, and you have 20. Ask them in person, so you can see his face.

    What are 10 deep questions for a boyfriend?

    Questions 49 to 58 in the Deep group. Ask five on one evening and five on another, since ten in a row feels like an exam. To start with one, try: What do you need to hear when you have failed at something?

    What are good random questions to ask your boyfriend?

    Set the picker above to all groups and press Next question; every draw is random. For a smaller pool, the Funny group (17 to 32) works best, because a silly question gets answered even when he is tired.

    What are good questions to ask your bf over text?

    Cute and funny questions, because they survive a one-line reply. Send one with your own answer attached, and leave the deep ones for when you are in the same room.

    From an answer to a pact

    Alpacto is the app for what comes after the answers. When something he said turns into a plan, it becomes a pact between you two, with a deadline, a standard of done and what it is worth in coins.

    120 questions to ask your partner, with six rules Would you rather questions for couples Couple questions game: 48 printable cards Questions to ask your girlfriend Questions to ask before marriage
    Sources on this page: Karen Huang, Michael Yeomans, Alison Wood Brooks, Julia Minson and Francesca Gino, “It Doesn’t Hurt to Ask: Question-Asking Increases Liking”, Journal of Personality and Social Psychology, 2017, 113(3), 430–452. How we write these pages, without a named author: our methodology.
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