Thanks for all the thoughts everyone. What I may end up doing is booking my ticket in F, then my friend's ticketing coach, in immediately calling and trying to use certain on his tickets. If I totally strike out, even after a few HUCAs and repeatedly asking nicely and explaining the situation, I'll cancel everything out and use certain for both of us.

Normally, I'd never go to all this trouble, but this guy doesn't fly very much and, while he's not "afraid" of flying, it's not a comfortable experience for him. In fact, I offered to join him on the trip because he doesn't like to be on airplanes alone. I'm just trying to make his travel experience a little more comfortable.