I watched this film for the first time a few months ago, and was completely dumbfounded about how this movie could've become such a big deal.
During the podcast, Amy more or less said that many scenes shouldn't work on paper, because of how outrageous and senseless Holly's actions are (for instance, when she breaks into Paul's apartment in the middle of the night). I thought this was a very good point, but I have to disagree with Amy's subsequent assertion that such scenes work regardless, because of Hepburn's performance. I, of course, agree that Hepburn is brilliant, but I non-the-less spend the majority of the film thinking "no one would ever do X," or at least, "no one would ever react that way to another person doing X."
I agree with everything Head Spin wrote - maybe it's just because I'm also a 26 year old white dude, but this movie did nothing for me..