When your best friend makes a crack about being a pain in the ass, by all means don't be so insensitive as to make a joke on a subject he's really sensitive about, namely, his ex-girlfriend.
Even though he really needs to lighten up and get over her.
In a hiring conflict between someone enthusiastic with four years of newspaper experience, and someone enthusiastic with zero years of newspaper experience, usually the one with the most XP wins.
In other words, someone else got the job; I am to just keep on searching.