30 Serious Questions to Ask Your Boyfriend


People may fall in love at different speeds. While some people fall in love in mere moments, other people have to gradually fall in love over several years. If you have had problems falling in love in the past, then you can use these questions to help your relationship. These 30 serious questions to ask your boyfriend will help you learn more about your guy and the things to avoid in your relationship if you want a stronger bond.

30 Serious Questions to Ask Your Boyfriend 

1. What made you break up with your last girlfriend?

Often, people will date the same type of partner over and over again. By learning why he broke up with his last girlfriend, you can figure out what the potential problems in your relationship will be. Learning the possible causes of a break up will help you prevent future problems and allow you to completely enjoy being with your boyfriend.

2. What did you like most about your last relationship?

Again, this is a great way to find out what he cares about. What makes him happy? More importantly, how can you make sure that he will remain in the relationship and in love with you over the long run?

3. Why do you think that I am the best girl for you?

Some intrinsic thing about you made him first start to like you. Use this question to figure out what made him so interested in being with you.

4. Will you marry me?

This question is best asked by a girl who has been in a serious relationship for quite some time and wants to know where everything is headed. Obviously, asking this question too soon could end up being rather off-putting for him. After you have been together for a few months or years, you can use this question to find out where everything is headed in your relationship.

5. What do you think about cheating in a relationship?

You need to know the answer to this question. Some guys like open relationships and don’t think that cheating is a big deal. Other men believe that it is a complete deal breaker. Before you fall head over heels in love with him, you need to make sure that he is always going to be faithful to you.

6. Will you love me forever?

Love is something that most people start to lose after months or years of a relationship. Temptations to cheat, work problems and small personality differences can make it easy to fall out of love. While there is no way to know for sure if the situation will change, at least this question will let you know that he plans on being there for you.

7. What makes you feel upset? How do you deal with it?

You do not want to unintentionally offend your boyfriend or make him feel upset with you, so you need to know what types of things make him upset. Plus, it is always a good idea to find out how to help him. If he failed a test or had a hard day at work, you could know how to make him feel better right away.

8. Have you ever cheated on your girlfriend?

Look him in the eyes as you ask this and pay attention to his mannerisms. If he has cheated, he may be ashamed to tell the truth. Listen carefully to his answer. While someone who cheated once may not always cheat again, it is a sign that you should be worried.

9. How would you react if I disappointed you in some way?

If he answers with anything other than, “I understand and we would work through it,” run the other way. Obviously, you don’t want to disappoint him, but he should understand that disappointments happen. If he responds by being angry or violent, he is not the type of person that you should be dating.

10. How long was your last relationship?

While your boyfriend does not need a track record of long-term relationships, it would be a good sign. If he has only had flings, I would not expect him to change all of a sudden.

11. How many kids do you want?

This is a good question to ask after you have been dating a while and an important one to ask before marriage. For your relationship to work, you will have to agree or compromise on the answer.

12. How do you handle arguments?

Learning the answer to this will help you learn how to react in an argument and what to expect.

13. What is your worst regret?

Everyone has regrets, and our mistakes our one of the things that define us as human beings. By learning from our mistakes, we can prevent similar problems from happening and become better people in the future.

14. Would you stay with me if I was pregnant?

If he says no, leave him. If you do not think he is being honest, you should also probably leave him. While you could have a child and break up (many parents do at some point, unfortunately), there is a difference between him abandoning you or him being a supportive partner and parent.

15. What is your religion?

People of different faiths marry all the time, but it is certainly something that you should know before you really commit to each other.

16. Do you like politics?

There are many different ways to learn about his likes and dislikes; this question is just another option that can help.

17. Do you believe in true love?

This could get an interesting response. Other options are to ask him if he believes in God, fate or love at first sight.

18. If you could change me in one way, what would you change?

This is a hard question to answer without offending someone, so be kind when you judge his answer.

19. How much do you love me?

This is a fun question to ask. If he does not know if he loves you yet, he may just joke around with his answer. Watch how he responds, and you will be able to tell if he really means it.

20. Do you feel happy when I am around?

If he is in love with you, the answer to this question ought to be yes.

21. What would you do if I cheated on you?

Hopefully, you will never have to find out if his answer is true. Cheating can put a great deal of strain on a relationship, so it is a good idea for both partners to avoid that temptation.

22. Where do you see our relationship headed?

If he wants things to be serious and more than a fling, he will already have an answer to this question. At any rate, it is something that you should talk about as a couple within a few months of dating.

23. Would you move if I was suddenly relocated for work right before we got married?

You would be surprised by how many people are ready to marry someone, but would still say no to relocating. While there is nothing wrong with not wanting to move, it is something that you should know before you commit to being with him for the rest of your life.

24. What are your hobbies?

While opposites may attract, it is always nice when there are a few things that you both have in common.

25. Do you believe in the supernatural?

This could refer to God and religion. It could also mean ghosts, spirits or otherworldly beings. It is a good question to use to get to know him better and see what he thinks.

26. What is your favorite meal?

As the lady, it is not your responsibility to prepare his meals. With that said, it is always nice to get a specially prepared meal from the person that you love. If you want to plan out a romantic dinner date with him or just surprise him after a bad day at work, then knowing the types of food that he likes can really help.

27. Do you believe in having an online relationship?

This could provoke an interesting conversation. With the rise of globalization, many people move to different states or countries for school and work. Long-distance relationships are becoming increasingly common. This questions will help you find out if he would be willing to have a long-distance relationship if you had to move for work or school.

28. What is your dream career?

As you two grow as a couple, you will be able to work on fulfilling dreams like this together.

29. What dreams do you have concerning your education?

This is another important question that will help you find out about where he wants to go in life and what he wants to accomplish.

30. What are your favorite sports?

If he is not interested in sports, you can always ask him what his favorite hobbies are. Finding out what he likes to do in his free time could give you more chances to get to know him better and fall in love with him even more.


  1. Hi there for question number 21 what can be your reaction I cheat on u . And in the righting part under neath the question it’s say if he would fight the guy or u as in me . What type of guy would hit a girl if she was to cheat and the parter hit her . ?

    • Abuse is never acceptable and should be reported immediately. You are correct, Stacey, it is never acceptable for a partner to hit their partner. Continue to remain mindful for people who are abusive or overly aggressive. Thank you for your comment, Stacey!


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