60 questions to ask your boyfriend (cute, funny and deep)

Guide · Updated 2026-11-07 · Pioneer Group ApS

These work just as well whichever of you is asking. Pick a section, ask one at a time and let the answers take you somewhere.

Cute

1. What did you notice first about me?
2. What's your favourite photo of us?
3. What's a song that makes you think of me?
4. What's the cutest thing I do without realising?
5. When did you first want to kiss me?
6. What's your favourite thing to do with me on a lazy day?
7. What nickname would you give me if you had to pick a new one?
8. What's your favourite memory from our first month?
9. What do you miss most about me when we're apart?
10. What's a date you'd love to recreate?
11. What's something I said that stuck with you?
12. What's your favourite outfit of mine?
13. When do you think I look happiest?
14. What made you sure about us?
15. What's something small I do that you love?

Funny

1. What's the most embarrassing thing that happened to you at school?
2. What's your worst haircut ever?
3. What would you do if you were invisible for a day?
4. What's your most irrational pet peeve?
5. What's the dumbest way you've ever hurt yourself?
6. Which film character are you most like?
7. What's a food you refuse to try?
8. What's your go-to karaoke song?
9. If you were an animal, which one would you be?
10. What's the worst gift you've ever given?
11. What's a weird habit you've never told anyone?
12. Who would play you in a film about your life?
13. What's the most childish thing you still do?
14. What would your last meal be?
15. What's the most useless thing you own and love?

Deep

1. What's something you're scared of that most people don't know?
2. What does a good day look like for you?
3. Who do you trust the most, and why?
4. What's something you wish you could tell your younger self?
5. When do you feel most confident?
6. What's the hardest thing you've ever had to do?
7. How do you like to be cared for when you're ill or stressed?
8. What's something you've never forgiven yourself for?
9. What makes you feel respected?
10. What does being a good partner mean to you?
11. What's a belief you hold that most people disagree with?
12. What are you most grateful for right now?
13. What's a goal you've been quietly working on?
14. How has your family shaped who you are?
15. What do you need more of in your life?

Future

1. Where would you like us to live one day?
2. What's a trip you'd like us to take?
3. How do you picture our weekends in five years?
4. What's something you'd like us to achieve together?
5. Do you want a pet, and what kind?
6. What's a skill you'd like to learn in the next year?
7. What kind of home do you want?
8. What does a good work-life balance look like to you?
9. What's a family tradition you'd like to continue?
10. What's on your bucket list?
11. What would you like us to save up for?
12. How do you want to celebrate our next anniversary?
13. What do you think we'll be like as an old couple?
14. What's something you want us to always make time for?
15. What's one promise you can make me today?

One a day

Rather than asking all 60 at once, try one a day. Pairbond asks you both a question every day, and the Getting to Know You deck is free. More lists: questions to ask your girlfriend and 100 questions for couples.