Questions to Ask Your Boyfriend: 100+ Fun, Deep and Flirty Ideas

109 questions to ask your boyfriend, by theme

Pick the theme that fits the moment, read one aloud and let the conversation wander. Every question below is a real card from one of our free couples games, so you can also play them as cards. Skip anything he (or you) don't feel like answering.

Getting to know him

From First Date Questions: easy, warm questions that work on a first date or a hundredth.

1. What do you do for work, and what do you enjoy most about it?
2. What's your hometown like, and what do you miss about it?
3. Are you a morning person or a night owl? Be honest.
4. What did you love doing on weekends when you were a kid?
5. What's your go-to comfort meal when you need cheering up?
6. Do you cook? What's the dish you're proudest of?
7. How do you usually unwind after a long day?
8. What was your very first job, and what did it teach you?
9. Which hobby could you happily talk about for hours?
10. Is there a food you used to hate and now love?
11. What matters most to you in a friendship?
12. How do you like to be supported when you're having a hard day?
13. What's something you're proud of that nobody ever asks about?
14. When you disagree with someone, what helps you talk it through?
15. What gives you energy, and what quietly drains it?
16. How much time on your own do you need in a normal week?

Deep questions

From Deep Questions for Couples: stories, values and the moments that shaped him. Save these for a calm moment.

1. What smell, song or taste instantly takes you back to being a kid?
2. Who outside your family helped shape who you are, and what did they give you?
3. What did you believe as a kid that turned out to be completely wrong?
4. What was a turning point in your life that looked small at the time?
5. Which younger version of you would you like to give a hug to, and what would you say?
6. What is a mistake from your past that you are oddly grateful for now?
7. How did your family show love when you were little, and how does that show up in you today?
8. What have you changed your mind about completely since you were younger?
9. How do you define success for yourself, and has that changed over the years?
10. What is one value you would never want to compromise on?
11. When do you feel most like yourself?
12. What does real rest look like for you, and what do you do when you truly need it?
13. How do you hope the people around you would describe you when you are not in the room?
14. What is something you have let go of that felt heavy for a long time?
15. What is a worry about the future that feels smaller once you say it out loud?
16. What would you try if you knew you could not fail?

Fun and silly questions

From Would You Rather for Couples and First Date Questions: daft dilemmas and what-ifs for when you just want to laugh.

1. Would you rather be able to… Fly anywhere you like / Turn invisible
2. Would you rather have… A dragon the size of a cat / A cat the size of a dragon
3. Would you rather… Talk to animals / Speak every language
4. Would you rather read… Minds / The future
5. Would you rather live with… A theme song everywhere you go / A narrator for your life
6. Would you rather be… Tiny for a day / Giant for a day
7. Would you rather be able to… Pause time / Rewind ten minutes
8. Would you rather never… Need sleep / Be hungry
9. Would you rather travel by… Teleporting anywhere / Time machine, any year
10. What would your superpower be, and how would you use it on a Tuesday?
11. What's your most useless talent? Demonstrations welcome.
12. Which movie could you quote from start to finish?
13. What's your karaoke song, and do you give it everything?
14. Which fictional world would you move to tomorrow?
15. What's your most irrational little fear?
16. If we started a band, what would we call it?
17. What's your party trick, or the one you wish you had?
18. What's the silliest thing you've ever been really competitive about?

Flirty questions (PG-13)

From Flirty Questions for Couples: sweet and teasing, never over the line.

1. What was the very first thing you noticed about me?
2. When did you first get butterflies around me, and what set them off?
3. What do I do that makes you smile without even trying?
4. When did you think, "Okay, I'm really into this person"?
5. What tiny habit of mine do you find secretly adorable?
6. What's your favourite way to hear me say your name?
7. Which song makes you think of me, and why that one?
8. How do you feel the second I walk into the room?
9. If you could freeze one moment with me, which would it be?
10. Who's the better flirt, you or me? Make your case.
11. Who do you think fell first, you or me? Defend your answer.
12. What nickname would you give me if I couldn't say no?
13. What's the surest way to make you blush? I'm taking notes.
14. Pretend we just met at a party. What's your opening line?
15. What's your dream date night with me, from start to finish?
16. What does a perfect cuddle on the sofa look like to you?
17. Which romantic place would you whisk me away to for a weekend?
18. What song should play for our next slow dance in the kitchen?

Questions about us

From Our Story: Memory Lane: how you met, your best moments and what you have learned about each other.

1. What do you remember about the very first time we met?
2. What was your first impression of me, and how close was it?
3. What was the first thing we ever laughed about together?
4. What did you tell your friends or family about me at the start?
5. Where were we when you first thought: I really like this person?
6. What was the moment you knew you were falling for me?
7. What's the funniest day we've ever had together? What happened?
8. What's an inside joke of ours, and where did it start?
9. What's a place that now feels like "ours", and what makes it ours?
10. When did I make you laugh so hard you couldn't stop?
11. What's a little habit of mine that you've grown to love over time?
12. What's something you've learned about me since we've been together that surprised you?
13. What's something about us that you're really proud of?
14. When did you realise you could really count on me?
15. What's one thing about us that you wouldn't trade for anything?

Questions about the future

From Deep Questions for Couples and Our Story: Memory Lane: dreams, plans and the life you picture together.

1. What is something you are looking forward to in the next few months?
2. Describe an ordinary day in the life you picture for yourself five years from now.
3. Where would you love to wake up in ten years, and who is nearby?
4. What is on your someday list that you have hardly told anyone about?
5. If you could ask your future self one question, what would it be?
6. What would you like to be doing on a random Tuesday twenty years from now?
7. Where would you love us to travel next, and what would we do there?
8. What's a new tradition you'd love us to start, just the two of us?
9. What's a skill or hobby you'd love for us to learn together?
10. Describe a perfect weekend for us a year from now.
11. Name three things for our bucket list that we should start ticking off.
12. What would a perfect day for the two of us look like in five years?
13. What do you hope we're still laughing about in ten years?
14. What are you most looking forward to in our future together?

Finish-the-sentence quiz

From How Well Do You Know Me?: he picks the answer that fits him, you guess. More on this below.

1. My favourite season is… Spring / Summer / Autumn / Winter
2. My favourite hot drink is… Coffee / Tea / Hot chocolate / Just water, thanks
3. When I'm stressed I usually… Go quiet / Talk it all out / Clean or organise / Reach for a snack
4. In the morning I am… Up at the first alarm / A dedicated snoozer / Slow, needs coffee first / Annoyingly chirpy
5. When I'm lost, I… Check the map / Ask someone / Trust my gut / Wander and hope
6. To recharge I need… Time alone / Time with you / Time with friends / Time in nature
7. My dream holiday is… A beach / A city break / A mountain trek / A road trip
8. The superpower I'd pick: Flying / Invisibility / Reading minds / Time travel
9. A little fear I have is… Heights / Spiders and bugs / Deep water / Speaking in public
10. My first impression of you was… Funny / Calm / Confident / Mysterious
11. The way I feel loved most is… Kind words / Time together / Thoughtful gifts / Hugs and touch
12. I'd describe us as… Best friends / Partners in crime / A cosy team / An ongoing adventure

How to ask without it feeling like an interview

• Ask while you do something else, like cooking, walking or driving. Side-by-side talk feels lighter than a face-to-face interview.
• Answer your own questions too. If only one of you talks, it is an interview; if you take turns, it is a conversation.
• Ask one follow-up before moving on, such as "What was that like?" or "Tell me more." It shows you were listening.
• Mix light and deep. Start with something silly, move on to a story, and keep a flirty one in your pocket for later.
• Let him pass, and stop when the answers get short. No scores, no judging, and no checking his answers against what you hoped to hear.

Try a simple rhythm: for every deep question, ask two light ones. The mood stays easy, and the deeper answers come more naturally.

Turn it into a game: How Well Do You Know Me?

If a list still feels like an interview, make it a game. In How Well Do You Know Me? each of you answers about yourself, then guesses the other's answer. The cards look like the quiz above, for example "My favourite hot drink is…" with four choices. Reveal the answers together, count the right guesses if you like, and talk about the surprises.

The game has 80 cards in four packs. Because it is about small, everyday things, it is also an easy way in for a newer relationship.

Which theme for which moment

There is no required order. Follow the mood.

Play it free online

1. Open How Well Do You Know Me? and choose Same phone or Online.
2. Choose a pack (or Mix for all four) and 8 or 12 rounds, then press Start.
3. Online, tap Play a friend, then Create table, and send your boyfriend the invite link or the 6-character code. He joins from his phone or computer, with no account needed.
4. Each of you picks your own answer, then guesses the other's. The answers are revealed together, so talk about the surprises.
5. Just want to talk? Open Deep Questions for Couples or Flirty Questions for Couples, read each card aloud and tap Next card.

Across the six games used here there are more than 500 cards to explore. For more ideas, try our guides to How Well Do You Know Me? questions, deep questions for couples and first date questions, or browse all games for couples.

Frequently asked questions

Related guides

• How Well Do You Know Me?How Well Do You Know Me? 48 Questions for Couples (With Answers to Pick From)
• Deep Questions for CouplesDeep Questions for Couples: 50+ Conversation Starters to Ask Your Partner
• Flirty Questions for CouplesFlirty Questions for Couples: 50 Sweet and Playful Ones to Ask Your Partner

All game guides →