99 Questions to Ask your Boyfriend – (2020 Update)

Disclaimer… Some guys aren’t as open as others when it comes to answering several questions at a time. Don’t ask all these questions at once.

Unless he agrees to it of course…

It may be a good practice to form these questions as a fun activity. Let him know that he can tell you to stop if he feels it’s getting too invasive.

So, take it slow. You don’t want to make these fun fact gathering questions the reason your relationship tanks.

As you read through them, take notes on how you would respond to these same questions and then Ask away. Enjoy!

13 Fun Questions to Ask Your Guy

1. What wishes did you have as a child? Have they changed?
2. If money wasn’t an issue in your life, what is the ultimate thing that you would like to buy?
3. What is your least favorite chore?
4. IF you hit the lottery what family member would you bless first?
5. If you could into a bird for a day, where is the first place you would go?
6. If Amazon reached out to you stating that they wanted to make an action figure toy of you what would it look like? What would be your special abilities?
7. What is one major goal in your life that you wish you could get a shortcut to pull off?
8. If you could trade your car in for whatever car you wanted free of charge (No Car Note) what car would that be?
9. Are you a cat or dog guy? Does it matter?
10. Of everything that has happened in your pass what is one thing that you wish you could relive?
11. If you had Bill Gates money what is something you would do that others look at as crazy or outlandish?
12. If you could only eat 4 things for the rest of your life, what would they be?
13. What is your dream vacation?

 Read Also: The TOP Ten Questions to Ask Your Boyfriend

22 Personal Questions to Ask Your Boyfriend

1. Is there anything that makes you cry besides physical pain?
2. What intrigues you the most about life?
3. If somebody said that they wish they could be you, would you recommend it or say “No you don’t? If “No” why not?
4. What is something about yourself that you don’t want anybody else to know about? LOL! I know you’re not going tell me that but what’s the next one closest to it?
5. When are you the happiest?
6. What grinds your gears the most? Is there anything you would recommend me not to do to not get you to that point?
7. Do you have a bucket list? Care to tell me about it?
8. What do you do for others that makes you the happiest?
9. At the end of life, what do you want others to remember about you?
10. Is there anybody in your family who you are uncomfortable around?
11. Who do you least like at work? Why?
12. If you could describe yourself using one word, what would it be?
13. Is setting goals for life important to you?
14. Are you a procrastinator? What do you do about it?
15. If you could put the last 30 days of your life in a book, what would you call this chapter?
16. The doctor has given the news that you have 5 more days to live… What would those last 5 days consist of?
17. If God gave you the ability to bring one person back from the dead, who would it be?
18. Are you into animals? What wild animal would you want as a pet outside of a cat or dog?
19. If you were to die and come back to life as an animal, what animal would you be?
20. Are there any goals you have in life that you want to achieve that you know you’re not doing anything to make happen?
21. What’s your attitude when things don’t go your way?
22. Who are you jealous of?

23 Questions to Ask Your Boyfriend About His Past

1.  Do you ever think it is an appropriate time to lie?
2. What was your most exciting vacation?
3. Have you ever broken up or severed ties with someone via text?
4. What are some of the things you’ve done that you don’t want your parents to know about?
5. What was your most embarrassing moment in high school?
6. If you could change one thing about the decisions you made as a teen, what would it be? How would it change the trajectory of your life?
7. What is the most courageous thing you’ve done concerning money or investing?
8. Is there a moment in your life that you wish you could revisit?
9. Who is the first person you would call when you receive good news?
10. Have you ever dissolved a friendship? Why?
11. What’s the earliest age in life you can remember events accurately?
12. How have you grown over the past three years?
13. What does your mother or father like to brag to others the most about you?
14. As a kid, what was your most favorite movie?
15. Which parent did you want to be the most alike when you were growing up?
16. Are there any family members you wanted to be like when you grew up when you were a kid?
17. What can you say about your life that has changed you for the better?
18. What can you say about your life that has changed you for the worse?
19. Have you ever done anything to a family member that you regret?
20. What is accomplishment in your life are you the proudest about?
21. As a kid, who was your favorite music artist to listen to? Are you still a fan?
22. Have you ever had your heart broken?
23. What’s the riskiest thing you’ve ever done?

Read Also: What to Say To Your Boyfriend to Make Him Happy

23 Questions to Ask Your Boyfriend About Relationship Views

1. What’s the biggest sacrifice you’ve made for a relationship?
2. What are some of the roles you feel that your ideal wife should fill?
3. Name one non-physical characteristic that I can change that will make me more attractive in your eyes.
4. Did your parents have the type of relationship that you would like to imitate?
5. In your life, what another couple’s relationship would you like to imitate?
6. Are you the type to be open to couple’s therapy if need be or are you against it completely?
7. What is your most favorite thing about being in a long relationship? What is your least favorite?
8. Would you prefer to live in the city or in a more rural country area?
9. Where do you get your ideas of what a relationship should be like from?
10. If you could spend a day with a loved one of your choice, what would that day consist of?
11. What are some of the most important takeaways that you have learned from past relationships?
12. Why do you think so many relationships these days fail?
13. What would your exes have to say about you if asked today?
14. Would you want my pregnancy by you to be planned or spontaneous? What would be your reaction if I tell you I’m pregnant surprisingly?
15. Do you mind changing diapers, or do you feel that is a woman’s job?
16. What’s your favorite female body feature?
17. What’s the kinkiest thing you like to do during sex?
18. Are there any sexual experiences you regret?
19. How should chores be handled around the house when living with your partner?
20. If you’re wrong about something we argue about are you open to apologizing?
21. What is your favorite part about dating?
22. What makes being your girlfriend worthwhile? What makes being your girlfriend not so cool?
23. Remove cheating from the list. What is an absolute deal breaker that would cause you to immediately consider a breakup?

12 Questions to Ask Your Guy About You and His Relationship

1.  What were your thoughts about me the first time that you laid eyes on me?
2. What is date we’ve been on would you say is your favorite?
3. What do I do that makes you feel loved?
4. As it pertains to spending money in a relationship is it ever ok to spend first and ask permission later?
5. Do you have any sexual fantasies that you want us to satisfy?
6. What are the top 4 things that make us a good couple?
7. When did you know I was the one for you?
8. What first interested you to me?
9. Is there anything I can change that would make me a better companion for you?
10. Do you think we have enough sex?
11. If we could redo any bad day in our relationship, which one would you choose?
12. Where do you want me to improve in my sex life with you?

Read Also: Is he the one for you?

6 General Questions to Ask Your Boyfriend

1.  What do you wish you could stop doing but can’t quite imagine life without at this present moment?
2. What are your thoughts on money and finances? Should you invest in something or just put it in a savings account?
3. What is something in your life that you learned the hard way but wish someone had schooled you on the subject earlier?
4. What do you feel is the most important subject to pay close attention while in school?
5. What societal norms do you think is the most damaging to most people?
6. If you could pick a popular or public figure to be like, who would it be?

Final Words

We have given you 6 subjects with many questions to keep your conversation with your boyfriend interesting. You will also find that they will strengthen your relationship.

So now that you have learned 99 Good questions to ask your boyfriend it’s time to put them to action!

As stated earlier, you should also be prepared to provide an answer to these questions. Don’t make your man feel like he is on the stand being interrogated by Johnny Cochran in the OJ Trial. Give him an opportunity to fire some questions at you too.

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