Blast from Your Past
Remember something from your childhood that you haven’t talked about with anyone for a while. Some interesting topics that might get his attention include cartoons that you used to watch, games that you played, family rituals or places you have been to. You can also tell him about incidents that happened in school or teachers that you didn’t like. Chances are pretty good that he had similar experiences as a child and he will open up.
Most people like a good tale, and many people have some interesting things to say about their families. Tell your boyfriend a story about something that happened in your family that was funny or weird. You don’t have to limit it to your immediately family, either. If you have an ancestor who did something out of the ordinary, voice it to your boyfriend. He will want to keep the discussion going by letting you know about his own family tree.
If you are comfortable in your relationship, tell your boyfriend a secret moment when you felt more embarrassed than ever. Not only will this let him know that you are at ease with him, it also lets him know that he can be confident in sharing such stories with you. Before too long, both of you will be telling each other stories about embarrassing moments that happened to each of you.
Ask for Advice
Everybody has a topic that he knows a lot about. Most people have several. Strike up a conversation about something that he is interested in by asking for advice about the topic. Ask him about the topic, and let him know that you are interested in making an educated choice. You can even caveat your inquiry by saying that you have a friend who is interested in the same topic. This not only lets him feel that you share a common interest but that you also trust his recommendations.