This one hits home for me. There was a really interesting San Francisco mayoral election about a year back. Gavin Newsom against Matt Gonzalez. Both liberals (we're talking about San Francisco), but Newsom was a moderate liberal, and Gonzalez was a Green.
Both of these guys were young, charismatic, and smart as hell. Anyway, my worldview was much more consistent with Newsom than it was with Gonzalez. But Matt Gonzalez was from my neighborhood. He was incredibly hip, had gone drinking with the Clash's Joe Strummer, was active in the arts, and was a brilliant debater. He lived in a rented, cheap apartment in the Haight with two roomates. He threw killer parties, had shaggy hair like me, and was clearly a guy that would be incredibly fun to hang out with.
Anyway, uncharacteristically, I voted with my heart and not my head. I voted for Gonzalez because he was so damn interesting, and was thrilled when he lost a narrow election to Newsom, because deep down I knew that Gavin would make the better mayor.
Very strange, and very unlike me, and I would imagine that this is the last time I do something like this. But it was a clear case of liking the liberal more than the conservative.