Questions to ask your boyfriend: 80 cute, funny and deep

80 questions to ask your boyfriend, sorted by mood: cute and fun ones to warm up, flirty questions for a night in, hypothetical and random questions for a laugh, questions to get to know him better, and the deep ones you have been meaning to ask. Every question works both ways, so answer each one yourself too.

80 questions ·

How to use these questions with your boyfriend

Pick one round, not the whole list. Read a question out loud, let him answer, then answer it yourself: the questions are written for two, and the second answer is where the conversation actually starts. Skip anything that does not fit tonight. If he gives a one-word answer, ask “why?” once and wait; that is usually enough.

Fun and cute questions to ask your boyfriend

Easy openers for a car ride, a walk or the first ten minutes of a date.

  1. Which holidays do you love celebrating the most – and why?
  2. What would your perfect day without a phone look like?
  3. If you could spend a day together inside a movie or TV show, what would you choose?
  4. If you could teleport somewhere together today, where would you go?
  5. If you could choose one superpower as a couple – what would it be?
  6. What thing from childhood still brings you joy as an adult?
  7. How do you like to celebrate your birthday?
  8. If you could live one day as other people – who would you be?
  9. Which movies or books can you come back to again and again?

Love questions to ask your boyfriend about the two of you

What he remembers, what he noticed, what he would relive. Expect at least one answer you did not know.

  1. If you could go back to one day in your relationship – which one would it be?
  2. What has surprised you the most since being together?
  3. What makes you feel proud of your relationship?
  4. What memory from your relationship always lifts your mood?
  5. What was the funniest situation from the beginning of your relationship?
  6. Which song reminds you the most of your relationship?
  7. What one word best describes you as a couple?
  8. What is one shared ritual you couldn’t imagine living without?
  9. What inside joke between you two always improves your mood?
  10. How have you changed since the day you met?
  11. What habit have you picked up from each other without even noticing?
  12. What do you remember from your first night together?

Flirty questions to ask your boyfriend

Kisses, looks and the compliments he wants more of. For a night in.

  1. What kind of kisses do you like the most?
  2. What makes you feel desired?
  3. Which looks between you completely disarm you?
  4. What do you love most about each other’s voices?
  5. What attracts you most to your partner besides their looks?
  6. What style of clothing do you like most on your partner?
  7. What scent reminds you most of your partner?
  8. What compliment would you love to hear from your partner more often?
  9. What words turn you on?
  10. How do you most enjoy being hugged or cuddled?
  11. How do you like to show desire?
  12. What gestures or words stimulate you the most?

Hypothetical questions to ask your boyfriend

A million dollars, a superpower, three hours left. Big scenarios, small revealing answers.

  1. You have a million dollars – what would you spend it on first?
  2. If the world ended in three hours, how would you spend them together?
  3. Imagine you both take a whole year off work. How would you most like to spend that time together?
  4. If you started a business together, what would it be?
  5. If you could know the answer to one question about your future, what would you ask?
  6. If you could start your career over, what would you try?
  7. If you were millionaires for a week, what would a typical day look like?
  8. You spend a week without phones or other distractions. How would you spend that time?
  9. You have 24 hours to make three shared dreams come true. What are you choosing?
  10. If you had 10 minutes to pack and leave for a spontaneous trip, where would you go?

Deep and serious questions to ask your boyfriend

Values, family, the things he has had to unlearn. Best later in the evening, one at a time.

  1. What do you think you’ve learned about love through past mistakes?
  2. What do you wish your partner understood about you more deeply?
  3. What does the phrase “true love” mean to you?
  4. How do you understand “boundaries” in a relationship? What do they mean to you?
  5. What does being a “good” partner mean to you?
  6. Do you understand “love” differently as you get older? In what way?
  7. How do you understand “emotional maturity” in a relationship?
  8. What was your idea of love before you met each other?
  9. How did your childhood shape the way you see love?
  10. Which past decisions have shaped you the most?
  11. What does balance between closeness and independence mean to you?
  12. What did you have to unlearn to build a better relationship?
  13. What did you learn about love by watching your parents’ relationship?
  14. What in your life has taught you the most about empathy?
  15. What was the bravest decision of your life?

Random, weird and dumb questions to ask your boyfriend

Fashion phases, teenage plans and the thing he can never resist buying. Guaranteed laughs.

  1. What was your most embarrassing fashion phase?
  2. What was your craziest idea as a teenager?
  3. What’s the dumbest thing you bought together and somehow still own?
  4. What’s the one thing you can never resist buying?
  5. What social trend just doesn’t make sense to you?
  6. What smell instantly takes you back to childhood?
  7. What usually goes through your mind right before you fall asleep?
  8. What weird habit did you only discover after you started living together?
  9. What animal best matches your partner’s personality, and why?
  10. What kind of pet would you love to have together?
  11. What words or jokes between you have a meaning no one else would understand?

Questions to ask a guy to get to know him

Who inspires him, what scares him, the rule he lives by. Good for a new relationship too.

  1. Who in your life genuinely inspires you?
  2. What scares you most in life?
  3. What’s something you love about yourself now that took you a long time to appreciate?
  4. What’s one rule or principle you try to live by?
  5. What are your biggest career goals right now?
  6. Which friendships matter most to you right now, and why?
  7. What do you miss most about being a kid?
  8. What city or country feels like a second home to you?
  9. What experience in life humbled you the most?
  10. What small pleasure during the day is important to you?
  11. What’s your favorite time of day, and why?

When you have run out of questions

These come from the free set in the coupleroom app, which has 2,500+ more sorted into 100+ topics and a Question of the Day that lands on both your phones. If he is the type who answers better in writing, Remote Mode lets you send him a question and see both answers once you have both replied. For a sillier evening, try the would-you-rather dilemmas or the couples quiz. If he wants to ask a few back, send him the questions to ask your girlfriend.

What are good questions to ask your boyfriend to get to know him?

Start with how he thinks rather than what he did: which time of day he loves, what he would do with a week off, which decision he would make differently. The fun round above is built from exactly those. Save family and values for when you have been talking a while.

What deep questions can I ask my boyfriend?

The deep round covers what love meant to him before you, what his childhood taught him, which boundaries matter to him and what he had to unlearn. Ask one, answer it yourself, and do not rush to the next.

Can I use these questions over text?

Yes, and some of them work better that way, because he has time to think. Send one a day rather than a list. In coupleroom, Remote Mode does exactly this: you send a question, both of you answer, and the answers open together.