Interesting Topics To Talk About With Your Boyfriend from Anne Jameson's blog

Ask him about his deepest secret

This is always a very interesting topic to talk about, because who doesn’t like to know about a person’s deepest secret. You will get him to reveal all the things he would normally never tell anybody. It could be an embarrassing story, a childhood tragedy, etc. Whatever it may be both of you will end up knowing the other person at a very deep level and might even end up having some laughs. This will give him a chance to get some things off his chest and sharing it with the person he trusts the most will also give him the confidence that his secrets are safe with you.

You could take turns, go back and forth so that both of you can get to share your secrets. It is a proven fact that sharing embarrassing stories brings people closer, and you offering to go first will help him make it easier to open up.

source