It never happened, but I thought I'd bring this one up because it looked liked the writers of the show were trying to set this up, but then were unable to carry through:
Jim and Jordan.
If you watch the few episodes Jordan was in at the end of Season 7, she seems to kind of like Jim. And then, I think in the last episode of the season, there is a tantalizing deleted scene where Jordan says in a "talking head" to the documentary crew that she thinks Jim is kind of funny, and she blushes and looks away.
It really looks like the writers wanted Jordan to be the "Cathy" of Season 8, who tries to seduce Jim, but I'm guessing Cody Horn couldn't/wouldn't return for another season?
I guess we'll never know.
But I think her character would've been much more interesting in Season 8 than Cathy's was.
Opinions are like tattoos-- everybody has one.