How can I help my boyfriend open up?

Good question. I have the same situation in reverse. My girlfriend won’t open up. I know she cares about me a great deal, but I am pretty darn good at getting others to talk about themselves, and I’m getting nowhere with her on that score. She is just coming out of a bad marriage where she was verbally abused. I would suggest consider his background. His family or ex may have given him the same treatment. I am asking deeper and deeper questions and it’s like it just comes to a halt. She has little to say. Questions, with her, that would start conversations, get a one or two sentence answer of finality. It is a long distance relationship as well. We text A LOT, but a telephone conversation rarely lasts more than 15 minutes. Although we can be together for 3–4 days and have a really good time. Don’t know if this is any help. I am beginning to wonder if I want to spend continuing time with someone who is incapable of carrying on a conversation, especially about deeper things in life.

I had a lot of trouble opening up to my last girl friend. When I realized it was endangering our relationship, I tried just saying everything that came to mind, in a stream of consciousness way. I was surprised that she was so interested in what I though of as gibberish. It was a very freeing experience.
Maybe you could do word association with him to get him to relax and be less guarded. One person says a word, and the other says the first thing that comes to mind. Go back and forth as fast as you can. I think it is a lot of fun. Actors do this to be less inhibited in rehearsa.

As a quiet guy myself, I’m betting that Skype is just not the best medium for reaching this guy. As much as he may love doing things with you, or hearing you share your thoughts and experiences with him, these Skype sessions are probably intensely uncomfortable. They’re going to make him even more self-conscious than usual and add an element of performance anxiety, like he’s got to cough up some meaningful converstaion now. That’s a real hard thing to do for guys like us.

My advice would be to keep your expectations low for these little sessions. Be prepared to do most of the talking, and when things get a little awkward, don’t make him feel like you’re anxiously waiting for him to deliver; find a gracious way to end the conversation without making him feel like he didn’t come through for you.

Believe me, for some of us, our lack of stuff to say doesn’t have anything to do with how we feel about our sweeties. “Opening up” may not be the right way of looking at it. He may not be holding back at all. Some guys inhabit a mental space that isn’t very verbal at all.

A long term separation can be mind numbing. Try to think back to some fun things you both like to do and discuss how fun it will be to do those things again when he returns. Gossip, latest news, favorites are always good stand by’s. You are in a tough situation for sure I hope the time passes quickly for you!

What about writing him some letters with lots of stuff he can answer or comment on?

A scalpel?

If you do video chat, do your next conversation topless.

This is pretty hard. It’s best to be physically near someone you love.
When I’d been living with my husband for, hmm about 24 years, I got myself a place in the city where I could sleep over when I worked 3 days in a row. Only an hour or two away, but the commute was rough.
Every night, at first, he would call to say goodnight. It was very romantic (at first). Then I’d go home for the long weekend.
After a few months, we’d both be tired when he called, and he wouldn’t have much to report, and I wouldn’t either, and my life up there was sort of not about him/me, and I very seldom called him first, and we’d have these tired silences on the phone. Eventually I was able to just go home, which made everything better.
I just don’t think the phone is the right medium. Or Skype either – each of you turns into a talking (or not-talking) head.
I think you need a plane ticket.

@susanc Very Very good comments on your experience. Most interesting that this happened after you had been married for so long. Thanks. Plane tickets do help enormously.

With a hachet

Try opening skype on your computers and just… leave it open. Don’t chat. Do other things. But if you’re, say, watching a movie you can comment to him. If you hear a funny joke, you can tell him immediately. You don’t have to be talking to be communicating. It’s like sitting next to each other on a couch—you can enjoy having the other person around without demanding they pay attention to you.

This is what my fiance and I do many nights as he lives halfway across the country.

@EmpressPixie This is a very very good idea. Thanks

Say something inappropriate and informal, will instantly break the ice.

I hate talking on the phone, especially cell phones, because of the delay. I don’t like not having visual cues with the person on the other side of the conversation. It has nothing to do with how I feel about the other person. I agree with @EmpressPixie‘s suggestion; that would work well for me. It would feel more natural.