Home Love 30 Personal Questions to Ask Your Boyfriend

30 Personal Questions to Ask Your Boyfriend


No matter how long you have been in a relationship, you can’t really know enough about someone unless you’re inquisitive enough to ask. Asking him personal questions allows you to know more about him than the things he would willingly divulge.


There are times when the personal questions you ask may hit a little close to home or he may uncomfortable to talk about. If you’re not in a serious relationship yet, it’s best to just let it be. On the other hand, if you really want to know more about a certain part of his life, it’s best to ask him this when you’re in private or when he’s feeling a little more chatty than usual.

Below are some personal questions you might want to ask your boyfriend to get to know him better.

1. What is your earliest childhood memory? A guy’s earliest childhood memory often makes an impact on who they become as an adult. However, don’t take it too heart too much as oftentimes a person’s earliest childhood memory is something mundane.

2. What is your relationship like with your dad? A father is a son’s first male role model. Who his father is can either become who your guy has become as an adult or who he doesn’t want to become.

3. What is your relationship like with your mom? A guy’s relationship with his mom can tell you a lot about his relationship with women in general. Guys who are loving and respectful towards their mom tend to be the same towards other women.

4. What is your relationship like with your siblings? Siblings are your first friends and often first rivals. Your man’s relationship with his siblings can tell you a lot about his thoughts on friendship and rivalry.

5. What did you like to do as a child? It’s nice to know how his childhood was like as this can shed light on the things in early childhood that made an impact on who he is now.

6. What was your favorite subject in school? You might be surprised to know about some childhood interests your partner has.

7. Who was your favorite teacher? Kids who love school usually have at least one favorite teacher that they idolize. It’s nice to talk about it as you reminisce about your childhood.

8. What movie, book, series, or music made a huge impact on you as a child? A child’s interests often helps to shape who they become as an adolescent, and therefore as an adult.

9. Who was your childhood best friend? Having a best friend in childhood is a sign that your boyfriend had a healthy social life.

10. Do you still keep in touch with your best friend from your childhood? If they’re still in touch, it could be a great way to ask him if you can meet his best friend. If not, the reason for their falling out could shed light on his personality as an adult.

11. Who was your first crush? It’s fun to know your boyfriend’s first crush because it gives you a glimpse of his “type” in girls.

12. Who was your first girlfriend? Romantic relationships shape our future view of relationships. Knowing his experience with his first girlfriend can shed light on his current relationship philosophies.

13. What was your relationship like? This where you’ll know what he was like in his first relationship – from first experiences to some naïve ideas that he has hopefully changed.

14. Why did you break up with your first girlfriend? You can know a lot about a person based on the first time they had their heart broken.

15. Who is that one girlfriend or fling that you would never forget? Naturally, this would take him some time answer for fear that you would get jealous or angry. But it can also let you know which relationship made a huge impact on him, why it changed his life, and what you can do to steer him towards a healthier view on relationships.

16. Why did it not work out with her? Oftentimes, the most unforgettable relationship we had is with someone who either nearly ruined our lives with how bad it was or with someone who was so great that breaking up with them caused us a lot of pain. This question can help you gain insight into how he realized he could do better or the circumstances that led them to part ways (if it was a good relationship).

17. What did you want to do right after high school or college? Did he take a gap year? Did he jump right into college or work? Did he take his time deciding what to do? These things let you know what he does when faced with a big decision that could impact his life in a big way.

18. What did you want to become when you grow up? Childhood ambitions stick with us for longer than we think. When you ask your man what he wanted to be when he grew up, the look on his face when he answers gives you a clue on whether he wishes he could still achieve that dream or if he abandoned that dream for other things.

19. What made you change your mind/what did you to to achieve that dream? If he says he has always wanted to be a doctor, but he’s now working as an accountant, there has to be something that made him change his mind, right?

20. What one part of your life do you wish you could change? This is when you can gauge whether he’s happy with his current life or if he’s unhappy. If he wants to change just little things, then you know he’s happy.

21. What one part of your life do you wish you could relive again? Reminiscing about the good times is cathartic, but it can also let you in on what past experiences he would like to relive again. Perhaps this can give you some ideas on future vacation activities.

22. Who do you idolize the most? Knowing more about his idol can help you know more about his view of the world. For instance, if he idolizes a particular musician, then the songs by that musician might tell you what he thinks of things. If he idolizes a historical figure, then it could mean he has dreams of being a heroic figure who would be remembered in history.

23. What quote from a movie or line from a song really resonated with you? As with above, if he doesn’t have a particular idol, a line that he remembers well can help you know his thoughts about certain things.

24. How do you feel about marriage? Naturally, this is something two people in a relationship should talk about at some point.

25. How do you feel about having children? As with above, having children is also up for debate. He might also mention how many kids he wants or how old he wants to be when he has his first kid.

26. What kind of husband or father do you think you would be? If he has a happy relationship with his father and his family, then he might say that he wants to be like his dad. Otherwise, he might say that he wants to be a different kind of man.

27. If you could have a conversation with someone who has long since passed, who would it be and what would you like to say? This is going to open a can of worms, but it can really tell you a lot about either regrets or a historical event that he’s curious about. He might want to talk to a loved one who has since passed on to just be able to converse with them again. However, he might also mention a historical figure that he would like to speak to so he can clear some facts up.

28. If you could say one thing to the person who truly hurt you, what would you say? This is where you can see his stance on forgiving someone who has hurt them immensely.

29. What do you wish you could say to your 16-year-old self? This is where you can learn about what he wishes he knew as a young man. This question can also shed some light on how he would handle a teenage son who is growing up to be just like him.

30. If you had the money to pack up and leave everything behind, would you do it? It’s a nice fantasy to think about, but it can tell you more about him than just his dream city to live in. If he jumps at the chance, then you know there are a lot of things he wants to leave behind. On the other hand, if he just wants to move to a new city without completely severing ties with his old one, then you know that he’s happy with where he is in his life.

The more your know about the man you’re in a relationship with, the better you will be able to handle any situation with him. So go on, ask away and learn more about your man each day!


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