Still, I think we can come up with some things that are both cool and undeniably useful. Case in point: One of the new LED-based lights, such as the Photon Fusion Headlamp ($70). It runs for 13 hours on one set of batteries, is very light, and puts out tons of light. Definitely cool.
Or, maybe one of the new all-weather jackets like REI's One Jacket ($200). This sheds light rain, blocks wind, breathes like a lungfish, and is comfortable across a wide range of temperatures. Cool when you want it to be, warm when needed.
How about a good altimeter watch? A useful thing, and also cool. If you think this relationship is a promising one, then maybe you'll spring for a Suunto Observer ($350). It's a rugged all-weather, full-function watch that includes barometer, altimeter, and digital compassBso he'll always find his way back to you! (AwwwwB.)
Of course, for that kind of dough you could replace the ratty backpack. That can be trickya pack is a pretty personal thingbut I bet he'd appreciate something like the Mountainsmith Terra ($260), a fine all-purpose backpack for hiking, climbing, and ski-touring.
So there you go. If he doesn't like any of these, dump the bum.