WHO: Jim Kirk and Shego
WHERE: Shego's room.
WHEN: Right now
WHAT: Jim was given a copy of his movie by Ariadne. But he doesn't have a DVD player and he doesn't really want to watch it alone. Enter: Shego.
It was probably really stupid to actually watch the movie that was supposedly about him. Who knew what was really on there and how it'd affect him to have to watch certain things from an outsider's prospective. But it was his own life and you know, he'd never really been one for self-preservation.
He hit a snag in the reckless when he realized he couldn't actually watch the movie without a DVD player and his quarters didn't come with one. They were obsolete by the time Enterprise was built. So he'd have to go find someone who had one, someone he didn't mind watching the movie with.
That was how he ended up next door, knocking on his Inmate's door. "Shego, c'mon, I have a surprise for you."