110 Questions to Ask Your Boyfriend (Deep, Fun, Cute and Flirty)

Whether you have been together three weeks or three years, the right question can still surprise you. Here are 110 questions to ask your boyfriend, sorted by mood so you can pick a few for dinner, a road trip, a late-night call or a slow Sunday text conversation.

How to ask questions without it feeling like an interview

• Ask one question, then really listen. Two good questions with long answers beat twenty quick ones.
• Answer it yourself too. It turns a quiz into a conversation.
• Follow up: “Why?”, “What happened next?”, “How did that feel?”.
• Read the room. Save the deep ones for a calm moment, not for when he is driving in traffic.
• No judging the answers. If he feels safe, the next answer will be more honest.

Questions to get to know him better (14)

1. What was the best day of your childhood?
2. Who was your hero when you were a kid?
3. What is a smell that instantly takes you back somewhere?
4. What did you want to be when you grew up?
5. Which teacher or coach changed something in you?
6. What is the most useful thing your dad or mom taught you?
7. What song did you have on repeat at sixteen?
8. What is your perfect lazy Saturday?
9. Which friend have you known the longest, and how did you meet?
10. What is a skill you are secretly proud of?
11. What food could you eat every day for a month?
12. What was the first thing you ever bought with your own money?
13. Where do you go, in your head, when you need to calm down?
14. What is a small thing that makes your day better?

Deep questions to ask your boyfriend (14)

1. What are you most grateful for right now?
2. When did you feel most proud of yourself?
3. What is something you have changed your mind about in the last few years?
4. What is a fear you do not usually talk about?
5. What does a good life look like to you?
6. Who do you need to forgive, or ask for forgiveness?
7. When do you feel most like yourself?
8. What is the hardest thing you have ever gone through?
9. What do you wish people understood about you?
10. How do you know when you need help?
11. Which of your habits would you like to break?
12. What did your last relationship teach you?
13. What does being a man mean to you?
14. If you could tell your fifteen-year-old self one thing, what would it be?

Fun questions to ask your boyfriend (14)

1. What is the weirdest food combination you secretly love?
2. Which fictional character are you most like?
3. If you had a walk-up song, what would it be?
4. What is the most useless talent you have?
5. What would your reality show be called?
6. Which animal would you be, and why?
7. What is the dumbest way you have ever hurt yourself?
8. If you could only eat one cuisine forever, which one?
9. What is your most controversial pizza opinion?
10. What would you do with a free day and zero responsibilities?
11. What celebrity do people say you look like?
12. What is the most embarrassing thing on your phone right now?
13. If you won the lottery tomorrow, what is the first thing you would buy?
14. Which song do you know every single word of?

Cute and flirty questions (14)

1. What did you notice first about me?
2. When did you know you liked me?
3. What was going through your head on our first date?
4. Do you remember what I was wearing when we met?
5. What is your favorite photo of us?
6. What is something I do that makes you smile without me noticing?
7. When do you think I look the most beautiful?
8. What was your favorite kiss of ours so far?
9. What nickname would you secretly like me to call you?
10. Which date of ours would you relive if you could?
11. What song makes you think of me?
12. What is the cutest thing I have ever done for you?
13. Did you ever plan something to see me that I never found out about?
14. What is your favorite thing about holding my hand?

Questions about your relationship (14)

1. What makes you feel most loved by me?
2. How do you like to be comforted when you have a bad day?
3. What is one thing I could do more often?
4. Is there something I do that bothers you but you never said?
5. What is your favorite memory of us so far?
6. How do you prefer to make up after an argument?
7. What do you think we do really well as a couple?
8. What is a tradition you would like us to start?
9. How much alone time do you need in a week?
10. Which couple do you admire, and why?
11. When do you feel closest to me?
12. What did you learn about love from your parents?
13. What is something new you would like us to try together?
14. How can I support you better when you are stressed?

Questions about the future (13)

1. Where do you see yourself in five years?
2. Which city would you love to live in, even for one year?
3. What does your dream home look like?
4. Do you want kids one day, and how many?
5. What is one thing you want to accomplish before thirty (or forty)?
6. Which trip do you want us to take together?
7. What would your ideal job look like if money did not matter?
8. How do you imagine a normal Tuesday when we are older?
9. What kind of old man do you want to be?
10. Is there a pet in our future?
11. What is a skill you want to learn in the next year?
12. How do you want to celebrate our next anniversary?
13. What does financial security mean to you?

Would you rather questions for your boyfriend (13)

1. Would you rather go back in time or see the future?
2. Would you rather have a cabin in the mountains or a flat by the sea?
3. Would you rather never use social media again or never watch another movie?
4. Would you rather have breakfast in bed or a picnic at sunset?
5. Would you rather be able to talk to animals or speak every language?
6. Would you rather go on a road trip or a city break with me?
7. Would you rather always be ten minutes late or always twenty minutes early?
8. Would you rather cook for me or have me cook for you?
9. Would you rather win an Olympic medal or an Oscar?
10. Would you rather live without music or without coffee?
11. Would you rather slow dance in the kitchen or sing karaoke together?
12. Would you rather know what I am thinking or have me know what you are thinking?
13. Would you rather relive our first date or skip ahead to our tenth anniversary?

Want more of these? We have a full list of would you rather questions for couples.

Questions for long distance or by text (14)

1. What is the first thing you want to do when we see each other again?
2. What did you have for lunch, and would I have liked it?
3. Send me a photo of what you are looking at right now.
4. What is the best thing that happened to you today?
5. What song should I listen to tonight to feel close to you?
6. Which of my messages do you reread?
7. If I could teleport to you right now, what would we do?
8. What do you miss most about me when we are apart?
9. What should we watch at the same time this weekend?
10. What would our perfect video call date look like?
11. Which day are you counting down to?
12. What is one thing you want to show me in your city?
13. Rate your day from 1 to 10, and tell me why.
14. What can I send you in the mail that would make you smile?

What to do with the answers

Keep the answers that made you laugh or that taught you something new about him. They are the raw material for a couple quiz, for a list of reasons why you love him or for an anniversary letter. And if you are the one being asked, our list of questions to ask your girlfriend works just as well the other way round.