OK, I think I'm getting a slightly better feel of where you're going with this now, and I definitely think I'm intrigued.

The strengths from chapter one continue nicely into this one, that's for sure.  Your grasp of Jessie's voice continues to be a highlight, and indeed, it's so strong it even helps make stuff that I might otherwise have a hard time buying, like the first-date jitters he starts to get near the end, feel very much believable for where he is right now emotionally and psychologically.  Which is itself another strong suit that carries over from the first part, a believable sense of Jessie trying to cope and move on with the events of the series, even as he finds himself not quite able to do so.  There's a push-pull to that aspect here I find really interesting, and I hope it receives further exploration as the story continues.