The Evil Anti-cool
Back when I was in Junior High School, before we had things like cellular telephony, metal tools or agriculture, I played Dungeons and Dragons. And marked myself as Unhip For All Eternity. Seriously. I think there's a mark on my forehead or something. All these millenia later, I still haven't completely outgrown the hobby, even though actually playing takes WAY too much time (since I've never been nerdy enough to place gaming ahead of a paying career) - so it's morphed into more of a literary/pop-culture thing. I go shopping for new games every so often, and peruse them to see how the hobby is evolving. There have been a number of interesting trends and fads over the years, like the rise of the interactive storytelling model of gaming, attempts to make roleplaying games as realistic as could be managed (or even more so) and the adoption of "open source" rules systems that allow people to create new settings without having to re-invent the wheel by creating their own mechanics. Even the artwork has changed with the times, with the popularity of Britney Spears over the past few years "inspiring" some illustrators to clothe their busty warrior wenches in bare-midriff mail crop tops and low-rider half-plate harness.
But I'm still amused by the most enduring aspect of role-playing - it's utter uncoolness, by ANY standard. Between the village idiot and a gamer geek, the idiot gets the girls, hands down. Take this line about the perils of misrepresentation in online dating from the November hardcopy issue of Wired magazine: "Your online paramour won't be thrilled to discover the 6-foot-tall althletic guy who 'loves entertaining' is an unwashed dungeonmaster in Birkenstocks (not that there's anything wrong with that)." Sure there isn't.
As much as many gamers themselves will tell you that the "unwashed" part is a stereotype born of a sad truth (pray you never learn first hand), I think they'd complain that the "Birkenstocks" crack is hitting below the belt.