I just started to go out with this really great guy, but he lives about an hour away. We talk on the phone every night, but after a while we run out of things to talk about and we have those really awkward silences. He's really fun to talk to, but we always run out of things to say. Help!
You also might try either shortening the conversation (end it early) and/or not talking everyday - I know from past relationships that things can get a little stale, and that might help. The only thing about that is you have to make it absolutely clear that it's not because you don't like him - you do, but would just rather not have the awkward silences.
I would suggest some kind of joke. Or something light to break the silence. I think it really depends on the direction of the conversation. You can always ask questions. Guys love to talk about themselves!