I always so feel embarrassed by the pretenses of my youth (i.e. anything I've ever done until a day before yesterday) and ask myself who the heck I think I am, trying to pull _____ off as if I'm the shit? And then I think, well, today I'm old/mature enough, and can proceed. Repeat two days later. When I was 20 I cringed at how dumb I must have looked puffing a massive cigar at 16. And when I was 22, I felt even more embarrassed by my smoking at 20. And the pattern continues. I wish I'd have ordered the cheaper beer last time I was out with friends, but tonight I'll feel it's alright....until tomorrow! OP: here's the lesson: just do what you have to do. Yes, you'll look like a bit of a douche and will feel somewhat self-conscious, but you need to start, and the sooner the better. Whenever someone tries acquiring a sophisticated taste they look dumb...until they succeed and then everyone else wishes they were as cool. I still cringe at my 16 year old self, puffing Churchill cigars and coughing my brains out on Park Ave. Ordering wines whose names I couldn't pronounce. Bragging about my crappy suits. Eating cheeses that made me gag. Going to the Opera and reading impossibly boring and difficult books (on the subway!). I called myself an "existentialist" (I didn't even know what that meant!) And all of this was with friends who wore tee shirts and talked sports.