20 Serious Questions to Ask Your Boyfriend

By on December 9, 2013

So you’ve been with your boyfriend for a few months (or even years) and you think you’re finally ready to dive into more serious conversations. But how can you be sure you’re asking the right questions? With these 20 serious questions to ask your boyfriend you’ll find out everything you need to know about the love of your life and the future for the two of you.


1. Why did your last relationship fail?

If you don’t already know, this is an important question. Did it fail because of him, or her? And what were the exact reasons? You may find out he was a cheater in past relationships or he had anger issues. Or it may be that he’s just a sweet guy who got used.

2. What did you learn from your past relationships?

If you don’t learn from past relationships, you’ll continue making the same mistakes and probably never end up in a valid, long-term relationship. Make sure your man learned a thing or two and knows what NOT to do.

3. Do you want anything to change in our relationship?

There is always something that can be changed, even if it is something little. If he says ‘no’, he’s probably just trying to flatter you and make you smile- but in the end, the same problems still remain. Work it out!

4. Have you ever cheated on a girlfriend?

Once a cheater, always a cheater. If he says yes, run for the hills.


5. Have you ever cheated on me?

Be careful with this question, as most people won’t own up to this terrible mistake. If he has, and admits it, you two will have a lot of talking and thinking to do.

6. Do you want kids?

Very important! If you want kids and he is absolutely against it, how far will your relationship really go?

7. How do you handle serious disagreements?

If the two of you have never had a serious argument, you need to know how he responds. Is he someone who lashes out without thinking, or does he remain silent until he can logically handle the situation?

8. What is your biggest regret?

You may find out your man is a goody-two-shoes, or you might find out he has done something terrible that frightens you. Obviously an important thing to know!

9. What would you do if I was in a serious accident and had to be taken care of for the rest of my life?

Tragedies such as this happens, and you need to know if your man would be willing to stick through them by your side.

10. What would you do if I got pregnant?

This is also important, as accidents such as these happen which affect the both of your lives for good. You need to know if he would stand by you and how he would react.


11.  Are you religious?

This question is really only important if religion matters to you. For example: an avid Christian who goes to church every Sunday probably won’t be in a very long relationship with an atheist who despises all types of religion.

12. What is the one thing you love most about me?

What is it about you that makes him feel warm and cozy on the inside? This is an important question- but it’s also one that will make you blush and smile.

13. If you could change anything about me, what would it be?

Maybe there’s a habit he’d like you to quit doing, like chomping your gum. Or maybe it’s something drastic like the color of your eyes. Find out what your man dislikes about you and see if it is something you can change, or something you should break up over.

14. Do you truly love me?

If his answer is ‘yeah’, or ‘yes’, or ‘sure’, then it’s probably not the real deal. You should expect a somewhat lengthy answer and at least a hug and a kiss afterwards.

15. Are you happy with me?

If he says anything other than ‘yes’, you may have a problem.


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

Would he lash out on you? Would he go beat up the man you slept with? You need to know what your man would do in such a serious predicament.

17. Do you see us getting married in the future?

That is the ultimate goal for a relationship, right? Therefore, any other answer than ‘yes’ should leave you worried.

18. If we were married and my career forced me to move, would you come with me?

Your husband should be willing to do anything for you, even if it means moving across the country or even to another country. Would you man go the distance?

19. Would you ever leave me?

Sometimes situations arise that are unforeseen (cheating, serious disagreements) that causes people to breakup. But if your man would be willing to leave at the slightest disagreement, you may want to rethink the relationship.


20. Where is our relationship going?

The most important of all questions: where is our relationship going. If it’s not moving towards living together, getting married, having kids, or something else along those lines, then you’re destined for failure. Your relationship should be moving forward- even if that means many years away. The point in this question isn’t to rush anything, but to simply see if your boyfriend is even thinking about future possibilities.