WTH, I was certain I made a post here.
Anyway, there's a significant time skip between the first time we play as Jess and Gerry and the second time.
Gerry can easily meet Grant and the others in that timeframe.
Then, when he drops Ellie at the VC, he looks for Jess, and they leave late for the boat because she couldn't find her CD player.
BTW, how expensive as a CD player back in 93? As I have some trouble believing Jess could have one.