Manhattan

Little sis: I don’t know. I’m just really confused. Like, how am I supposed to know what I want in a guy? You know? Like, what’s your perfect guy?
Big sis: One with 6 weeks to live.
Little sis: Huh?
Big sis: Nevermind… God, that would be great, though.

–1 train platform, 23rd St

Girl #1: Actually, my mom ran into your grandmother the other day near here.
Girl #2: Oh, really? Was my grandmother nice to her or was she a raving bitch?
Girl #1: Oh. I don’t know.

–7th & Christopher

Hobo to male passerby: Spare change? Anything helps — God bless.
Passerby: Get a job.
Hobo: Get on your knees and give me a job!

–72nd & Broadway

Girl: Why are you wearing cowboy boots?
Guy walking other way: I just got off work.
Girl, to friend: Did that guy just call me a whore?

–East Village

Overheard by: James Triggs

Princess: So are you, like, bored?
Man: No. I’m homeless.
Princess: Oh!

–Port Authority

Suit #1: So, how long did your five-minute meeting last?
Suit #2: A fucking hour.

–John St, between Cliff & Pearl

Guy: Did you try rebooting?
Chick: Of course.
Guy: Because that’s the first thing you should try doing when you–
Chick: –Look, half the guys I’ve dated have been in tech support. I’ve picked up a hell of a lot more than just VD. I know about rebooting.

–NYU

Overheard by: ctrl alt delete

Minnesota girl: Like, when I come to New York I want to do something, like, crazy and fun!
Guy: Well, listen, you ran into the right guy, because I am, like…
Girl and guy in unison: Mr. Crazy Fun!
Guy: Exactly. Like, tonight I’m thinking about starting off at this place called a hookah bar. Have you ever heard of one?
Girl: No! What is it?
Guy: Well, it’s this place where you smoke tobacco in Jordanian water pipes!
Girl: Wow.

–Koronets Pizza, 110th & Broadway

Overheard by: Wyatt

Yuppie: You know, that’s a very expensive beer you’re not drinking.
Girlfriend: Can’t we have one night where you don’t quote American Psycho?
Yuppie: Oh, he bought her Chardonnay. Don’t worry, I’m not a Chardonnay guy.
Girlfriend: Whatever. Just don’t nail-gun me in my sleep tonight. Again.

–Iggy’s on Rivington

Man: Don’t you want to go to the water?
Woman, wiping something off her arm with a napkin: No. I’ve had enough poop for today.

–Central Park South, between 5th & 6th

Overheard by: Victor