170+ Best Questions To Ask Your Boyfriend

Gwen Adams

Questions to ask your boyfriend

Your boyfriend must have had many experiences, and achievements before you came into his life. You may also want to know his favourite memories and opinions on some matters. To know all of this you would need the right list of questions, or you can also hit a good pick up line to make them feel good. These questions will help you understand why he’s the right match for you.

Questions to ask your boyfriend

Fun Questions to Ask Your Boyfriend

Asking some funny questions is always better than asking random questions. From favorite childhood memory to cartoon characters these questions can lead to fun revelations about your boyfriend.

Fun Questions to Ask

  1. What was one toy you always wanted as a kid?
  2. What’s your favorite thing to do when you are getting bored?
  3. You have to marry a fictional character. Who do you choose?
  4. What was your favorite T. V show as a kid?
  5. What was your favorite movie as a kid?
  6. What’s your favorite ice cream flavor?
  7. What’s your favorite type of music?
  8. What is your hidden talent?
  9. Who is your favorite superhero?
  10. What’s the best dish you can cook?
  11. What’s the weirdest thing that you enjoy?
  12. When you were a kid, what career did you want to have?
  13. Do you or have you ever had, a fear that seems silly?
  14. Who would you be most excited to get a postcard from?
  15. What is your idea of a perfect Sunday afternoon?
  16. Have you ever snooped on a partner?
  17. Would you rather meet an alien or a ghost?
  18. What is the best present you’ve ever received?
  19. What is something you think is vastly overrated?
  20. What did you and your friends do for fun in middle school?
  21. What is the most interesting piece of trivia you know?
  22. Who is the funniest person in your life?
  23. What’s the best pick-up line you know?
  24. Have you ever gone to summer camps?
  25. What’s the most stupid thing you have done that you are proud of?

Questions About You

Knowing things about your boyfriend is good but seeing him talk about you is even more exciting. Know what opinions your boyfriend has about you with these interesting questions.

Questions About You

  1. What do you like about me?
  2. What do I do that makes me interesting?
  3. Have you ever felt embarrassed in front of me?
  4. Am I changing you in any way?
  5. What’s the weirdest thing about me?
  6. What’s the positive change you have had after I came into your life?
  7. If you could ever choose one of my qualities what would it be?
  8. What do you think I can do well in the relationship?
  9. What’s something you would like to teach me?
  10. Do I show up in your dreams and fantasies?
  11. When did you got attracted to me for the first time?
  12. What kind of personality do you think I have?
  13. Am I good at keeping secrets?
  14. Do I contribute to resolving our issues respectfully?
  15. Where have you always wanted to go with me?
  16. What habit do you wish I had quit?
  17.  Do you think I fight fair?
  18.  Have you observed any changes in me since the time we met?
  19.  If you would change my name, what would it be?
  20.  What’s the happiest memory of me?
  21. What’s the first thing you noticed about me?
  22. Have I enabled any bad habits in you?
  23. Have I been there for you when you needed me?
  24. Have you ever felt insecure about me?
  25. What’s the biggest impact I have had on you?

Questions About Him

Know more about him than his memories. Ask some simple real-life guy questions to know your boyfriend better. With these questions, you might be able to understand more about his personal life.

Questions About Him

  1. What’s one thing you can’t live without?
  2. When you sleep, do you prefer your room cold or hot?
  3. Have you ever had a fictional dream girl?
  4. What are you afraid of?
  5. Are you a dog person or a cat person?
  6. What’s your favorite drink?
  7. What’s something that is seemingly normal but grosses you out?
  8. What is your zodiac sign?
  9. What’s your favorite book?
  10. What is your favorite food?
  11. How would you describe your relationship with your family?
  12. What’s your dream vacation?
  13. What’s the biggest lie you have ever told?
  14. Do you have a best friend?
  15. What makes you doubt yourself?
  16. Have you ever stolen anything?
  17. What is your ideal date?
  18. What’s your favorite art style?
  19. Do you believe in love at first sight?
  20. Are you friend with any of your exes?
  21. What was your favorite subject in middle school?
  22. Who was your role model growing up?
  23. Do you believe in a soul mate?
  24. What’s your favorite season?
  25. What’s the worst injury you have ever had?

Cute Questions to Ask Your Boyfriend

Want to see the cute side of your boyfriend but not sure how? Just ask some cute freaky questions and see how it goes. Check out some cute questions that you can ask your boyfriend.

Cute Questions to Ask Your Boyfriend

  1. What’s the best Halloween dress you have ever had?
  2. What’s your favorite candy?
  3. What’s the most embarrassing thing that you have ever done?
  4. You are a superhero, what’s your superpower?
  5. How do you feel about dating younger girls?
  6. If you had to choose between being blind or deaf, which one would you go for?
  7. What are the qualities of a great girlfriend?
  8. Where do you see us in 10 years?
  9. Can I steal your phone to play a game on it, please?
  10. What’s your favorite scary movie?
  11. Do you have a nickname for me?
  12.  How would it feel if I kissed you now?
  13. Do you have any superstitions?
  14.  Have you ever cuddled with your pillow?
  15.  If someone called your girlfriend stupid, how would you react?
  16. What would happen if we broke up tomorrow?
  17. Where were the best places to go on our first date together?
  18. Is there anything I can do to make you feel better right now?
  19. What is your theme song?
  20. Do you have a special talent?
  21. What does your family think about us being together?
  22. What kind of makeup do you like on me?
  23. Do you have any scars on your body?
  24. Do you notice a difference in the way I talk to you when we are together and when we are apart?
  25. Do you collect anything?

Love Questions to Ask Your Boyfriend

Boyfriend questions don’t always have to be general. You can also know the romantic side of your boyfriend by asking relationship questions or romantic questions. So, ask these intimate questions to Feel the love in your boyfriend’s answers.

Questions About Past Relationships

  1. Have you ever kissed someone under mistletoe?
  2. What is the difference between love and being in love?
  3. Do you believe in fate?
  4. Is there someone that you never want to hurt?
  5. When did you know for sure that you loved me?
  6. What is the sexiest thing a partner can wear?
  7. How would you react if I told you that I want to be with someone else?
  8. Will you hold my hand when we walk under the street lamp on a foggy night in the future?
  9. What is your love language?
  10. Have you ever been in a love triangle? How did it end for you?
  11. If I turned into an angel, what would I be?
  12. What do you think is the best way to know if someone is the one for you?
  13. What was your most romantic experience with a partner that is different from all others?
  14. What are the most romantic things you’ve done?
  15. What qualities do you appreciate in a partner you’d like to date?
  16. What do you value most in a relationship?
  17. If I asked you to write me a love letter, what would it say?
  18. Can you name three things that make an intimate relationship work?
  19. How can couples prevent boredom in their relationships?
  20. Do you feel a lot of pressure to become involved in a long-term relationship?
  21. What is something you must say to make your boyfriend feel closer to you?
  22. Do you know what makes your partner happy?
  23. What’s the most important quality in a relationship that is not so obvious?
  24. What is the most romantic way to ask someone out?
  25. What is one of your favorite love quotes?

Questions About Past Relationships

Sometimes knowing the past can be a good way to understand a person better. By knowing things about your boyfriend’s past relationship, you can figure out what you can do better. So here are some questions about your boyfriend’s previous relationship to help you with that.

Questions About Past Relationships

  1. When was your first relationship?
  2. What was your girlfriend like back then?
  3. Was your ex-girlfriend kind and considerate?
  4. Did she mention anything about her past relationship with you?
  5. How did the breakup work out?
  6. Do you think that things have changed since then?
  7. Did you ever break up with your girlfriend before now?
  8. How was each relationship different from the other one, and how do those differences affect your current relationship right now?
  9. What would your ex-girlfriend say that she likes about his current boyfriend compared to his previous boyfriend (if she is dating someone right now)?
  10. How would your ex-girlfriend describe you?
  11. What do you think about the boy that your girlfriend had been seeing previously?
  12. What do you think about your previous girlfriend?
  13. Was there any way to help them last together forever?
  14. Did your ex-girlfriend talk about the problems she was having with you?
  15. How did your ex-girlfriend deal with these problems compared to how you deal with them now?
  16. How your partner handled her past relationship can teach a lot about how you should deal with problems that matter most to you.
  17. What are the things that went wrong in your previous relationship?
  18. Why did you stay together for so long?
  19. What do you think about your previous girlfriend?
  20. Would she say anything about him to help him out?
  21. Did you have a happy ending with your ex-girlfriend?
  22. Did your family members know about your past relationship?
  23. How did the breakup work out with her?
  24. Is there anything you would like to change with your previous ex-girlfriend if given the chance?
  25. What are some things she did right in your previous?

Questions About Life

Know what makes your boyfriend feel more lively and understand his perspective towards his life with deep questions. Don’t ask weird questions, just keep it simple. Ask questions like the one mentioned below to have a meaningful conversation about different aspects of life.

Questions About Life

  1. Who’s your role model?
  2. When was a time that made you feel proud of yourself?
  3. Have you broken any bones?
  4. What is your very favorite color and why?
  5. Can you describe your life in five words?
  6. What makes you anxious?
  7. What’re the things you enjoy the most about your life?
  8. Have you ever been to therapy?
  9. Can you tell me a time when something unexpected happened to you?
  10. What’s your favorite moment of your life so far?
  11. What’s the biggest risk you have ever taken?
  12. What’s the best piece of advice you have ever received?
  13. Have you ever met a famous person in your life?
  14. What are the things that went wrong in your previous relationship?
  15. What’s the best advice your parents ever gave you?
  16. Do you think that money can buy happiness?
  17. Have you ever been in jail before?
  18. What do you want to accomplish in your life?
  19. How important is love in a relationship, and do you think it is possible to be in love with more than one person at the same time?
  20.  What do you think is the most important prerequisite in a relationship?
  21. What do you think is the most important thing in a relationship?
  22. Do you think that traveling can make people happy in a relationship or make them very happy?
  23. Is there something that you’re afraid to talk about in your relationship?
  24. Do you think it is possible to be happy in a relationship if you’re not 100% faithful to your partner?
  25. Do you consider yourself emotionally strong enough for a healthy relationship?

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Knowing your partner is one of the key aspects of a healthy relationship. It sounds pretty tough but you can know your boyfriend pretty well if you hit the right chord. You can ask some interesting questions that can help you have some interesting conversations. So, go ahead and ask the questions mentioned above to know your boyfriend better.


What is a playful question?

Playful questions are just quirky and flirty questions that you can ask your partner?

What are some good questions to ask a long time boyfriend

You can ask some intimate and deep questions to a long-time boyfriend. You can check out our post too for different sets of questions.

What question you should never ask your boyfriend?

You should never ask negative or dark questions to your boyfriend. Because it can make him uncomfortable.

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