60 Questions to Ask Your Boyfriend

Good questions do two things: they make him talk, and they make you both laugh. Here are 60 questions to ask your boyfriend, sorted from fun to deep to flirty, so you can match the mood instead of jumping straight to the heavy stuff. Pick a section, take turns, and answer your own questions too.

📌 Save to Pinterest

Fun questions to ask your boyfriend

Zero pressure. Good for the car, the queue, or when dinner is taking forever.

  1. What is the most useless talent you have?
  2. If you could only eat one cuisine for a year, which one?
  3. What is a movie you pretend to hate but secretly love?
  4. Which fictional character would you want as a best friend?
  5. What was your most embarrassing haircut?
  6. What would your walk-on song be?
  7. If you were a kitchen appliance, which one would you be?
  8. What is the worst piece of advice you have ever followed?
  9. Which app on your phone would you defend to the death?
  10. What is your most irrational fear?
  11. If we started a band tonight, what would it be called?
  12. What is the strangest thing you believed as a kid?
  13. What would you do with a free Tuesday and no responsibilities?
  14. Which of your friends would survive longest on a desert island?
  15. What is one food you refuse to try?

Questions to get to know him better

For newer couples, or long-term ones who assume they already know the answers.

  1. What did you want to be when you were ten?
  2. Who is the person you call first with good news?
  3. What does a perfect Saturday look like for you?
  4. What is a small thing that instantly improves your day?
  5. Which of your habits did your family give you?
  6. What is a skill you wish you had learned earlier?
  7. What was the last thing that made you laugh out loud alone?
  8. What do you do when you need to reset?
  9. What is a compliment you have never forgotten?
  10. Which place feels most like home to you?
  11. What is a hobby you would pick up if time were no object?
  12. What is your favourite way to spend money on yourself?
  13. What is a tradition you would like us to have?
  14. Who in your life do you admire, and why?
  15. What is a story you tell everyone at least once?

Deep questions to ask your boyfriend

Save these for a quiet moment. One at a time, and let the silences happen.

  1. When do you feel most like yourself?
  2. What is something you are still learning to forgive yourself for?
  3. What does being a good partner mean to you?
  4. What is a fear you have about the future?
  5. How do you want to be supported when things go wrong?
  6. What did your parents get right, and what will you do differently?
  7. What is something you have never told me because it felt small?
  8. What has our relationship changed about you?
  9. What would you regret not doing in the next five years?
  10. What makes you feel loved without anyone saying a word?
  11. When have you felt closest to me?
  12. What is something you need more of from me right now?
  13. What is a belief you held strongly that has changed?
  14. What do you hope people say about you when you are not in the room?
  15. What are you proud of that nobody asks about?

Flirty questions to ask your boyfriend

For later in the evening. Answer with actions if words fail.

  1. What was the first thing you noticed about me?
  2. What do I do that you find attractive without meaning to?
  3. Which of my outfits is your favourite?
  4. When did you last catch yourself staring at me?
  5. What is your favourite way to be kissed?
  6. What would you plan if you had one night to impress me?
  7. What song makes you think of me?
  8. What is the most romantic thing you have ever wanted to do for someone?
  9. Where would you love to be surprised by me?
  10. What is a compliment you would love to hear from me more often?
  11. What is something new you would like to try together?
  12. What instantly puts you in a flirty mood?
  13. What is your favourite memory of just the two of us?
  14. If tonight had no plans, how would you want it to go?
  15. What is one word from me that makes you melt?

How to turn the list into a night

  • Guess first. Before he answers, say what you think he will say. A correct guess earns a point; a wrong one costs a sip or a dare.
  • Mix the sections. Two fun, one deep, one flirty. Repeat.
  • Let the wheel decide. Spicy Trivia asks a couples question every third round and spins a wheel of rewards and dares after each answer. Add your own dares before you start.

More lists: questions to ask your girlfriend, couples quiz questions and would you rather for couples.

Frequently asked questions

What are good questions to ask your boyfriend to get to know him?
Ask about the small things: who he calls with good news, what resets him after a bad day, what he wanted to be at ten. Specific questions get real answers where big abstract ones get shrugs. The getting-to-know-him section above is built around that idea.
How do I ask deep questions without it feeling like an interview?
Take turns, answer your own question first, and never ask more than one deep question in a row. Turning it into a game, with a small forfeit for passing, keeps it playful. Spicy Trivia does exactly this with its couples rounds.
Is there a game that asks these kinds of questions?
Yes. Spicy Trivia is a free browser game for two: trivia questions plus couples questions your partner asks and judges, and a wheel of rewards and dares after every answer. Date night mode keeps it playful; After dark turns up the heat.