Edit:
I think it perfectly captures post-college life in the 90s.
I agree. It came out when I was a junior in college, and I loved it in large part because it resonated so much with my life then. I watched it again recently, and it didn't hit me the same way and I did find Hawke's character whiney (something I didn't see at all earlier);
however, I still do love the film for what it captures and for what it captured from my life then. Apart from Hawke, I like all the characters - they feel real to me. Actually, now that I'm thinking of it, even whiney Hawke feels real - I had a boyfriend in college who was very much like him, constantly moaning about his philosophical angst.