100 Questions to Ask Your Boyfriend, From Fun to Deep

Whether you have been together three weeks or three years, there is always more to learn about each other. Good questions are the fastest way there. They turn a quiet dinner into a two-hour conversation and remind you why you like this person in the first place.

The 100 questions below start light and get deeper as you go. You do not need to ask them all. Pick a few from a section that matches the mood.

How to ask so it does not feel like an interview

• Answer them yourself too. Take turns. It is a conversation, not a quiz.
• Follow up. The best part is the second question: “Why?” or “What happened next?”
• Match the setting. Fun questions work on a road trip. Deep questions work on a slow walk or late at night.
• Skip freely. If a question lands wrong, laugh and move on.

Fun questions to ask your boyfriend

1. What is the most useless talent you have?
2. If you could eat only one meal for the rest of your life, what would it be?
3. What is the weirdest food combination you secretly love?
4. Which fictional world would you most want to live in?
5. What would your entrance song be if you were a wrestler?
6. What is the most embarrassing thing you did as a teenager?
7. If you had a warning label, what would it say?
8. What is a movie you can quote almost word for word?
9. If animals could talk, which would be the rudest?
10. What is the strangest thing you believed as a kid?
11. Which celebrity would you want to be stuck in an elevator with?
12. What is your go-to karaoke song?
13. What would you do with a free day and no responsibilities?
14. What is the worst haircut you ever had?
15. If you started a business tomorrow, what would it be?

Would you rather questions

1. Would you rather live by the beach or in the mountains?
2. Would you rather be able to fly or be invisible?
3. Would you rather go on a road trip or a cruise?
4. Would you rather know the future or change the past?
5. Would you rather have a fancy dinner out or a pizza night in?
6. Would you rather give up music or movies?
7. Would you rather live in a big city or a small town?
8. Would you rather be famous or rich and unknown?
9. Would you rather have a cat or a dog?
10. Would you rather spend a week camping or a week in a luxury hotel?

Getting-to-know-you questions

1. What was your childhood like?
2. Who were you closest to growing up?
3. What did you want to be when you grew up?
4. What is a smell that takes you straight back to childhood?
5. What is your favorite way to spend a Sunday?
6. What is something most people do not know about you?
7. What is the best trip you have ever taken?
8. Who is your best friend, and how did you meet?
9. What is a hobby you have always wanted to try?
10. What is a book, film or album that changed how you think?
11. What are you most proud of?
12. What is your biggest pet peeve?
13. Are you a morning person or a night owl?
14. What does your ideal weekend look like?
15. What is the best advice you have ever been given?

Romantic questions

1. What was your first impression of me?
2. When did you know you liked me?
3. What is your favorite memory of us?
4. What is something I do that makes you feel loved?
5. What is your favorite thing about our relationship?
6. Where would you take me on a dream date?
7. What song reminds you of us?
8. What is something small I do that you love?
9. What was going through your mind on our first date?
10. How do you like to be comforted when you have had a bad day?
11. What is your love language?
12. What is one thing you want us to do together this year?
13. When do you feel closest to me?
14. What is a moment with me you would replay if you could?
15. What made you want to keep seeing me?

Deep questions to ask your boyfriend

1. What are you most afraid of?
2. What is something you have changed your mind about in the last few years?
3. When do you feel most like yourself?
4. What is a mistake that taught you something important?
5. What does a successful life look like to you?
6. Who has had the biggest influence on who you are?
7. What is something you wish you could tell your younger self?
8. What do you need more of in your life right now?
9. What is something you struggle to talk about?
10. How do you handle stress?
11. What does trust mean to you?
12. What is a value you would never compromise on?
13. What is something you are still trying to forgive?
14. When was the last time you cried, and why?
15. What makes you feel respected?

Questions about the future

1. Where do you see yourself in five years?
2. What is one big goal you want to reach?
3. Where would you most like to live someday?
4. How do you feel about marriage?
5. Do you want kids, and if so, how many?
6. What kind of home do you picture for yourself?
7. How do you think about money: saver or spender?
8. What is a place you want to visit before you are 50?
9. What would you do if money were no issue?
10. How do you want to spend your retirement?
11. What traditions do you want to keep or start?
12. What does a balanced week look like to you?
13. How do you picture us in ten years?
14. What is something you want to learn in the next year?
15. What do you want people to remember about you?

Questions about the relationship

1. Is there anything you wish we did more often?
2. How can I support you better?
3. What is something we do well as a couple?
4. How do you prefer to handle disagreements?
5. What is one habit of mine that bugs you, honestly?
6. How much time alone do you need each week?
7. What do you think we should celebrate more?
8. Is there anything you have been wanting to tell me?
9. What is one thing we could try that is new for both of us?
10. What does a perfect day together look like for you?
11. How do you feel when we are apart for a while?
12. What is a relationship you admire, and why?
13. What makes you feel appreciated by me?
14. What is one thing you would never want us to stop doing?
15. What is our next adventure going to be?