Hi crew!
My new man friend + I are bad communicators.
How can we talk about difficult stuff?
A guy tried to chat me up at a bar + he got really upset, with me.
We didn't talk about it + even though we are close + involved, we have never broached the subject of where we are.
We spend a weekend together, all the time + don't talk for a day or two afterwards.
Do we talk or do I walk?

Well, start talking about your feelings, your dreams, your hopes.
Talk about the things you like and dislike.
Talk about books, movies, sport and politics.
Talk about your childhoods and families.
Talk about your day, what you did and who you spoke to.

The trick is to listen while the other person is talking (I mean really listen - don't be waiting to speak) and ask questions - be genuinely interested.

Don't only talk when there is something difficult to say or to confront.

Talk to each other as if you like each other and have a desire to find out who you really are.

It's hard to say whether you can mend this communication issue, you'll have to just try and see if it works.

If you know something has bothered him though, that you have done, it might be best for you to broach the subject and address it head-on.

For example, "Dave, I would guess that it might have made you feel uncomfortable with that guy approached me at the bar. I just wanted to let you know, I don't feel it's appropriate to be rude if someone shows an interest in me - it's flattering. But I did tell him I am with you, and I turned down his offer of a drink. I would do the same if you were not there - I'd let the guy know I have a boyfriend and politely decline."

You might also mention to him that the silence between you is of concern, and ask if he has suggestions for both of you to get more comfortable speaking up. This is a lot better than being accusatory like, "hey, you don't say anything - it's so annoying!" Let him know your goal is to be closer, but that you think that communication between you needs to increase and see whether he'll work with you on it.