I know how you feel, loki. I've been switching between 38s and 40s for a while. I have to use a belt with the 40s but the 38s feel like tight leggings on me. Oh and finding 40/32 jeans is hard, I think they assume if you have a 40" waist you must be built like a little teacup.
But let's see, hmm... five years ago, summer 2004, I had just finished my sophomore year of college, just changed majors to what I eventually graduated with... BUT I was poor, living with my parents (got a duplex later in the year), and had a kind of shitty social life.
I'd say I'm happier now.