Well, the jam-session today went better than expected. Even though we were only two guitarists, it was nice to try again. We don't exactly have that many songs in common that we can play, but that can be fixed with time. He did, however, have one song of his own that he thought could be improved, so we tried that a few times. The first time, he just played it so I could get an idea about the feel, tempo and rhythm of the song. Then after that, he asked me, a less experienced guitarist, to try improvising over it, so I did (thought "what's the worst that can happen, right?"). The first attempt didn't go so well. Second attempt went a bit better. Third attempt, nailed it down. The end-result sounded really nice and melodic, especially considering that I'm not very used to improvising and soloing.

I'm definitely looking forward to jamming with him again!