Questions to ask your boyfriend: 160 he'll want to answer

Which questions to ask, and when

The same question lands differently three weeks in and three years in. Use this to pick a section:

How to ask without it feeling like an interview

• One or two per evening. A list of twenty fired in a row feels like a form. One good question can last an hour.
• Answer first. "I've been thinking about the best year of my life. Mine was when I was nineteen. What's yours?" Going first makes it a swap.
• Side by side for the deep ones. In the car, on a walk, cooking. Many people find hard questions easier without eye contact.
• Follow up. The first answer is the headline. "Why that one?", "Who was there?", "What happened after?" get the story.
• Never use the answer against him later. If a question about his ex or his fears comes back in an argument, he'll stop answering honestly.
• Let him pass. "Ask me another time" is a fine answer. Come back to it in a month.

Fun questions to ask your boyfriend

Light, quick, good for a long drive or a slow evening. Many of these turn into a debate, which is the point:

1. What's your most controversial food opinion?
2. Which fictional character do you think you'd actually get along with?
3. What's a skill you'd learn overnight if you could?
4. What's the most childish thing you still do?
5. If you could only eat one cuisine for a year, which one?
6. What's the worst haircut you've ever had, and who's to blame?
7. Which TV show could you rewatch on a loop?
8. What's the strangest thing you believed as a kid?
9. If you had to get a tattoo tomorrow, what would it be?
10. What's an hour of your life you'd like back?
11. Which three people, alive or dead, would you have over for dinner?
12. What sport would you be in the Olympics for, if effort counted and talent didn't?
13. What's the most embarrassing thing on your phone right now?
14. Which smell do you secretly love that most people hate?
15. What would you do with a completely free Wednesday?
16. What's a rule you always break?
17. What's the best thing you've ever found on the ground?
18. Which decade would you live in if you could pick?
19. What's your go-to karaoke move: the song, or the dance?
20. If animals could talk, which ones would be the rudest?
21. What's a word you love the sound of?
22. What would your autobiography be called?
23. What's the most impressive thing you can cook with five ingredients?
24. Which household chore would you happily do forever?
25. What's your most irrational fear?
26. What's the best advice you've ignored?
27. Which app would you delete first if you had to lose one?
28. When did you laugh hardest at exactly the wrong moment?
29. If you were a restaurant, what would be on the menu?
30. What's a small luxury you'd never give up?

Questions to get to know your boyfriend

For the first months, or for the parts of his life you've never asked about. Each one has a story in it:

1. What were you obsessed with at twelve?
2. What's a smell that takes you straight back to being ten?
3. Who was your best friend growing up, and are you still in touch?
4. What did you want to be when you grew up, and what happened to that?
5. What was dinner like in your house as a kid?
6. What's the best summer you've ever had?
7. Which teacher do you still think about?
8. What's the first thing you ever bought with your own money?
9. What's a place you've been that you'd go back to tomorrow?
10. What's something your family always did that you thought everyone did?
11. What was the hardest year you've had so far?
12. What are you better at than people would guess?
13. What's a book, film or album that changed how you think?
14. Who do you call when something good happens?
15. What does a really good day at work look like for you?
16. What's a compliment you've never forgotten?
17. What's something you taught yourself?
18. What would your friends say is your worst habit?
19. What do you do when you need to be alone?
20. What's a risk you took that paid off?
21. What did you think your life would look like at this age?
22. Which of your parents are you more like?
23. What's a tradition from home you'd like to keep forever?
24. What makes you lose track of time?
25. Who taught you the most about how to be an adult?
26. What's the best thing about where you grew up?
27. Who in your family are you closest to, and why them?
28. What's a job you've had that taught you something unexpected?
29. What do you do on a Sunday when nobody needs you?
30. What's something you're saving up for, or dreaming about?

Deep questions to ask your boyfriend

Save these for when there's time and nobody's tired. Ask one, then listen:

1. What's something you believed at twenty that you don't believe now?
2. When did you last feel really proud of yourself?
3. What's a mistake you're glad you made?
4. What are you most afraid people think about you?
5. What does success look like to you, honestly, not on paper?
6. Who do you miss?
7. What's something you've never told anyone because nobody asked?
8. What part of growing up do you still carry around?
9. When do you feel most at peace?
10. What's the hardest thing you've ever had to forgive?
11. What do you wish you'd been told at fifteen?
12. What's a topic you avoid, and why?
13. What would you do if you knew nobody would judge you?
14. Which of your values would you never bend on?
15. What does being a good man mean to you?
16. Who has hurt you the most, and what did it teach you?
17. When was the last time you changed your mind about something big?
18. What do you need when you're struggling, even if you don't ask for it?
19. What are you still trying to prove, and to whom?
20. What do you think happens after we die?
21. What would you want people to say about you at the end?
22. What's a part of yourself you're still working on?
23. What makes you feel respected?
24. What's something you regret not saying to someone?
25. What's something you'd like to be braver about?
26. What does a good friend do that most people don't?
27. When did you last feel lonely?
28. What's a belief from your family you've kept, and one you've dropped?
29. What do you think you'll understand at fifty that you don't now?
30. What's a moment that changed the direction of your life?

Romantic questions about the two of you

Once you've been together a while. These are the ones that make him think about you while he answers:

1. What did you get wrong about me at the start?
2. When did you know you wanted to keep seeing me?
3. What makes you feel loved?
4. What's something I do that you've never told me you love?
5. What's our best day so far?
6. Which chore would you most like me to take over?
7. When do you feel most like a team with me?
8. What's something we argue about that doesn't really matter?
9. What's something I say that hurts more than I realise?
10. What's one thing you'd like us to try that we haven't?
11. Which of our in-jokes is your favourite?
12. What's an opinion of mine you've quietly started to share?
13. What did your friends say about me at the start?
14. When have I surprised you?
15. What's something you'd like more of from me, and something less?
16. What's the first sign that I've had a bad day?
17. What's a present from me you still use?
18. What's a moment you felt really close to me that I might not remember?
19. What would you like to do for our next anniversary?
20. What do you think we're good at, together?
21. What's something we do that you'd never want to stop?
22. When did you last feel I really listened to you?
23. What's a fight we had that you think made us better?
24. What would you tell a friend about how we met?
25. What's something about me you had to get used to?

Serious questions about the future

The ones that tell you whether you're heading the same way. Most are fine a few months in; the ones about money, children and marriage are for when it's serious:

1. Where would you live if work didn't matter?
2. What's a trip you want to take before you're forty?
3. What would you like to have learned in five years?
4. What does a good weekend look like when you're sixty?
5. What do you want your home to feel like?
6. What would make you want to leave this city, or stay in it for good?
7. What's something you want to own one day?
8. How important is it to you to live near your family?
9. What would you change about your job if you could?
10. What are your deal breakers in a relationship?
11. What did your parents teach you about money, and what would you do differently with us?
12. Do you want children, and how sure are you?
13. What does marriage mean to you, if anything?
14. What would you need to feel settled?
15. What's one thing you want us to have done together in ten years?
16. How do you like to spend birthdays, yours and mine?
17. What would a perfect year off look like?
18. How do you picture splitting the chores in a shared home?
19. What's a goal you'd want me to push you on?
20. Which day of the year should be ours, and what do we do on it?

Questions for a long-distance boyfriend

For calls when you've run out of news. They pull the other city into the conversation:

1. What did today smell like where you are?
2. What's the best thing you ate this week?
3. Who did you talk to most today, apart from me?
4. What's something you saw today that you wanted to show me?
5. What's the first meal we're having when we're together?
6. If you could spend one hour of my day with me, which hour would you pick?
7. What's playing in your room right now?
8. What's something you've started doing since we've been apart?
9. When do you miss me most?
10. What's the loudest sound where you are right now?
11. What do you want to do on our first evening, before anything else?
12. What's the plan for closing the distance, as you see it now?

Flirty questions to ask your boyfriend

Playful, not crude. Good for a text when you're apart, or a slow evening in:

1. What's the first thing you remember about me that you didn't tell me at the time?
2. What did you want to do at the end of our first date that you didn't?
3. What's a song that makes you think of me in a way you wouldn't say at dinner?
4. What's the way I say your name that you like best?
5. What's a nickname you'd secretly like me to call you?
6. Which photo of me do you look at when you miss me?
7. If we had a whole day with no phones, what would we do?
8. What's a date you've been planning in your head?
9. What compliment do you think I don't hear enough?
10. What would you do if I turned up at your door right now?
11. What's a plan for the two of us you've been keeping to yourself?
12. What's the oddest thing that's reminded you of me lately?
13. What would you like me to text you at a random moment tomorrow?

Turn the questions into a game

Sometimes it's easier to ask when a card or a game asks for you. Our free question cards have decks for a light evening, a closer one and a long-distance call, and How well do you know me? turns it into a quiz: you each answer about yourself and guess the other. The cards are for one phone you pass between you. The quiz also works on two phones, so you can play it from different cities, and Would you rather? is there for a lighter round. For a digital gift that asks the questions for you, these two do it well:

If you'd rather tell him something than ask, try our cute things to say to your boyfriend, and for more ideas for him, the digital gifts for your boyfriend.