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20 Really Good Questions To Ask Your Boyfriend

Your relationship with your boyfriend may have reached the point where you both feel comfortable with each other. These questions you can ask—not all at once of course—to enliven things and have some fun.


How many serious relationships have you been in? This is a good one to ask at the beginning of the relationship. It will give you a sense of his emotional security.

Have you ever had your heart broken? This is another good one. Although few of them will admit, heart break has a very deep and lasting impact on a man.

What do you want out of life? A general question to be sure. However, you may be surprised at how he answers it.

Where do you see your career going? You will get a glimpse at how happy he is in his current job—whether he takes it seriously and intends to stick with it and seek promotion.

Do you like the way I dress? We tend to be really self-conscious—especially about the way we dress. He may be reticent to tell you what he really thinks. Ask him flat out. And prepare yourself for an honest answer.

Are you ever attracted to other women? There is little doubt that he is, but you shouldn’t feel threatened. He will probably try to avoid answering. Coax him a little.

Do you think I’ve gained weight since we met? We shouldn’t get too comfortable girls!

What do you think about us living together? The question is better asked after you’ve been together for a while.

Do you like my friends? You don’t have to like everything about each other’s friends. But if you want to keep both him and them in your life you should get a sense of who he doesn’t like and why.

Have you ever been jealous over me? It’s nice to feel that your man has been jealous over you—admit it.

What would you think if I went back to school? Some guys have a real problem with women who are more educated than they are. If you’re thinking of going to grad school, you should determine whether he is one of them.

Do you find me attractive in the morning? Another question that he is unlikely to be straightforward about. But you should try to get him to do so. We are completely unmasked in the morning and are therefore likely to be at our most unpleasant. You will be able to gauge from his face how unpleasant when he responds to the question.

Would you like to meet my parents? If you live far from your parents, you will need to arrange a special trip just to get this done. If he says yes, it can shift the relationship into a completely new level.

When will I meet your parents? Don’t panic if he’s evasive. He may have issues with his folks that he would prefer to work out before he introduces you to them. Again, it is a big deal if you have to make a special trip to meet them.

Would you like to have children some day? This is another question that is best asked after you’ve been in the relationship for a while. It can be a delicate matter, so you don’t want to be pushy.

If you could change one thing about me, what would it be? He may give you the predictable answer of nothing. Or, he may be honest and tell you the truth. You will never know unless you ask.

What would you say to my changing careers? If you’re seriously thinking about doing so, it will affect his life as much as yours.

What do you think of spending Christmas together? Christmas is a time for family. If you’re thinking of spending it together, you will either have to go together to your family’s place or his or you make it a Christmas of just the two of you together.

Do you mind that I have male friends? This can be a real problem for some guys. You want to get as straight an answer as you can about it.

If we got married, would you ever consider becoming a stay-at-home dad? If you have the kind of career that keeps you busy and in the office a lot, then you really should consider this as an option. It is the kind of question you want to ask your boyfriend when you think he’s ready to speak seriously about marriage and the future.

As you can see, these questions can give you real insight into your partner’s mind. They can be a great way to put a bit of a spark into the evening.

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