I recently discovered Overheard in New York, thanks to Trey Givens. It’s basically a blog of snippets of strange and/or stupid conversation overheard in New York City.
Some are philosophical:

Guy: Do you know what the word “ontological” means?
Chick: Yeah…I have seen it before…
Guy: Yeah. Me too.
Chick: Is it like an orange?
Guy: Yeah…Well, it’s something weird like that.
Chick: I know what you mean.
–Hungarian Pastry Shop, Amsterdam Avenue

Some are just funny:

Professor guy: I was going to give you all a quiz today. But then I realized that it was Valentine’s Day. You’re supposed to do something for the people you love on Valentine’s Day. And of course, I love all of you very much. So…I decided to give you the quiz on pink paper instead!

–Columbia University

Some reveal remarkable ignorance:

Woman #1: So I decided to celebrate turning 50 by traveling to Tibet.
Woman #2: Tibet? Where’s that? London?
Woman #1: …No, it’s near China and Russia.
Woman #2: Oh. It’s not like I don’t like to travel but I went to Mexico once and it was stupid.
–4 train

And:

Teen guy #1: Well, I’m French.
Teen girl: I’m German.
Teen guy #2: Well, I’m from Spain so I guess we’re all from Europe.
Teen guy #1: Spain isn’t in Europe.
Teen girl: Dude, yes it is. Europe is like its own continent.
Teen guy #1: I was talking about Europe the country, not that little
island with England on it.

–McDonalds, St. Marks & 3rd

Then there’s my personal favorite example of subjectivist stupidity:

Girl: I feel like if your vagina is wet enough, you won’t get AIDS.

–Kitchenette Uptown, Amsterdam Avenue

I’d say that nothing could possibly top that, but I’m sure that I’ll read worse soon enough.