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Questions to Ask Your Boyfriend

Good Questions to Ask Your Boyfriend

Asking your boyfriend questions is a great way to not only learn more about your special guy, but also to show him that you are interested in him as an independent person-not just as your “boyfriend.” Although there are a ton of different questions you can ask, we have created a list of our favorite serious and silly questions to help you get started! Feel free to put a personal twist on any of these 25 questions and think of new questions if you are inspired by this list of questions to ask your boyfriend!

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11 What is your favorite way to spend your free time?

Why this is a great question to ask your boyfriend: Your guy obviously loves spending time with you, but he also has a life outside of your relationship. Getting to know what he likes to do will help you learn more about him and can help give you some great date ideas.

1. What is your favorite way to spend your free time?

22 What is your least favorite way to spend your free time?

Why this is a great question to ask your boyfriend: Knowing what your guy doesn’t enjoy doing is the best way to ensure that you will never plan a date that he is secretly dreading!

2. What is your least favorite way to spend your free time?

33 What is your earliest memory?

Why this is a great question to ask your boyfriend: This is a fun question to ask because it gives you insight about your boyfriend’s life before you were his girlfriend. Early memories often shape who we are later in life so you may even gain an understanding as to why he does certain things today!

3. What is your earliest memory?

44 Do you think you are outgoing, introverted, or something in between?

Why this is a great question to ask your boyfriend: Even though you may think you know whether your boyfriend is outgoing or not, his answer may surprise you and reveal that he is more complex than you thought!

4. Do you think you are outgoing, introverted, or something in...

55 What do you value most in a friend?

Why this is a great question to ask your boyfriend: You are his girlfriend, but you also want him to see you as a friend he can count on. If you don’t already demonstrate his most valued friendship quality, think about ways that you can start.

5. What do you value most in a friend?

66 What qualities do you dislike in a person?

Why this is a great question to ask your boyfriend: Although opposites can attract, relationships are sustained by sharing certain values. If your boyfriend hates assertiveness, and you are full of opinions, this question may reveal that you two will run into some issues.

6. What qualities do you dislike in a person?

77 What is your least favorite food?

Why this is a great question to ask your boyfriend: Now you know what not to make for him if you’re in the mood to treat him to a home cooked meal!

7. What is your least favorite food?

88 If you could be a girl for a day, would you?

Why this is a great question to ask your boyfriend: Some guys are curious about girl things, some guys aren’t. Odds are that if he would want to try it out, he is an open-minded guy who is willing to listen to you talk about lady things that might make other guys uncomfortable!

8. If you could be a girl for a day, would you?

99 Where would you travel to if you had a free flight anywhere?

Why this is a great question to ask your boyfriend: It’s always interesting to hear where people would like to visit if they had the opportunity. If you both would like to go to the same place, maybe this would be a good time to suggest a romantic holiday!

9. Where would you travel to if you had a free flight anywhere...

1010 What is your spirit animal?

Why this is a great question to ask your boyfriend: This is a fun question and he may say something that surprises you. If he thinks he’s a lion, but you think he’s a kitten, you may want to keep your opinion to yourself if you want to re”mane” on his good side!

10. What is your spirit animal?

1111 Do you think it is better to regret doing something, or regret not doing something?

Why this is a great question to ask your boyfriend: This is a classic question that always leads to interesting conversation. If he seems willing, you can ask him what his biggest regret is and if/what he learned from it.

11. Do you think it is better to regret doing something, or reg...

1212 What do you think your best physical feature is?

Why this is a great question to ask your boyfriend: It may be hard for him to answer this since guys generally think less about physical appearance than girls. If he has no answer, be sure to boost his confidence by telling him your favorite features of his!

12. What do you think your best physical feature is?

1313 What do you think your best character trait is?

Why this is a great question to ask your boyfriend: Obviously he has a lot of great characteristics since you decided to date him, but it is interesting to find out what he thinks his best character trait is.

13. What do you think your best character trait is?

1414 If you could be immortal, would you?

Why this is a great question to ask your boyfriend: This is another great question that will lead to a long conversation, maybe even a debate!

14. If you could be immortal, would you?

1515 Do you prefer urban cities or rural towns?

Why this is a great question to ask your boyfriend: See if you can guess his answer!

15. Do you prefer urban cities or rural towns?

1616 When was the last time you were embarrassed?

Why this is a great question to ask your boyfriend: This question will probably lead to a funny answer, but if he is still painfully embarrassed about the incident, don’t forget to remind him how great he is!

16. When was the last time you were embarrassed?

1717 What is the grossest thing that you have ever witnessed?

Why this is a great question to ask your boyfriend: Depending on his answer, you may regret asking!

17. What is the grossest thing that you have ever witnessed?

1818 What political issue are you most passionate about?

Why this is a great question to ask your boyfriend: If he is interested in something you don’t know much about, you now know that you have an opportunity to learn from him!

18. What political issue are you most passionate about?

1919 What is your favorite TV show?

Why this is a great question to ask your boyfriend: Hopefully he likes something you like because remote control arguments are annoying!

19. What is your favorite TV show?

2020 Do you prefer girls who are “glammed up” or natural?

Why this is a great question to ask your boyfriend: While you should always dress and accessorize yourself in the way that you are most comfortable, it doesn’t hurt to know his preference!

20. Do you prefer girls who are “glammed up” or nat...

2121 Who was your first crush?

Why this is a great question to ask your boyfriend: This question will probably lead to some funny stories!

21. Who was your first crush?

2222 Do you believe in ghosts?

Why this is a great question to ask your boyfriend: If he does, ask if he has a spooky story to share!

22. Do you believe in ghosts?

2323 What did you want to grow up to be when you were little?

Why this is a great question to ask your boyfriend: How cute is it to imagine him as a youngster?!

23. What did you want to grow up to be when you were little?

2424 How did you meet your best friend?

Why this is a great question to ask your boyfriend: When you date a guy, you need to interact with his friends. He will appreciate that you demonstrate interest in his closest friendship.

24. How did you meet your best friend?

2525 How do you think society will be different in 50 years?

Why this is a great question to ask your boyfriend: This question is sure to lead to an interesting conversation!

As you can see from this list, there are a ton of questions you can ask your boyfriend. It’s important to ask each other questions to learn more about each other and demonstrate that you are interested in each other. We hope you enjoyed this list of 25 questions to ask your boyfriend, and don’t hesitate to think of even more questions!

25. How do you think society will be different in 50 years?
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