I'm contemplating doing what most of you decry b'c I'm flying one leg where I will happily take my upgrade, but meeting someone else who has no status at my connecting airport and will fly with her the rest of the way. I've been told by the elite desk and a gate agent that there's no way to specify flight segments for upgrade--you request all (each way) or nothing (each way).

So if I'm upgraded away from my companion, I will attempt to regain my seat next to her by offering the new occupant of my EC seat the opportunity to move up to FC.

The only other option I see is to selflessly uncheck "upgrade requested" and fly coach both legs.