Preppy guy #1: How was that bar in Midtown?
Preppy guy #2: Dude, it was awesome… It was full of hot chicks.
Preppy guy #1: If it was so great, why did you text me eight times in one hour and are now standing next to me pissing at this bar?
–Restroom, Delancey Bar
Overheard by: Al
Emaciated goth/punk guy: Hey, do you know where a CVS is?
Passerby suit: I don't know what that is…
Passerby preppy girl: Are you looking for a CVS?
Emaciated goth/punk guy: Yes!
Preppy girl: Well, there's a Duane Reade right there, it's like, the same thing.
Emaciated goth/punk guy, matter-of-factly: I know, it's just impossible to steal from Duane Reade.
Preppy girl: Oh.
Emaciated goth/punk guy: I'm really poor.
Preppy girl: Okay.
Emaciated goth/punk guy, cheerful: Thanks anyway!
Preppy girl, also cheerful: You're welcome!
–Columbus Circle
Overheard by: Hannah
Preppy gay guy: I thought she already had cancer?
Preppy fag hag, dawning realization: You're right! She did… definitely.
–Bleecker & Grove
Overheard by: jams
Preppy guy #1: I want to go to my country house this weekend.
Preppy guy #2: I was going to ask you if you wanted to go to my beach house with me.
Preppy guy #1: …Listen to this conversation we’re having right now.
–26th & Lexington
Overheard by: raic
Preppy girl #1: So my mom was like, “I’m serious, stop being a retard or I’ll send you back.”
Preppy girl #2: Really? She’d send you back?
Preppy girl #1: Yeah, for being a retard. What the fuck.
Preppy girl #2: I dunno, man. What the fuck.
–Barnard college
Overheard by: Alix Griffith-Rand
Preppy guy: What's that stuff around the rim of your martini glass?
Trendy girl: Uh…I dunno, it looks like cum.
Preppy guy: Uh… can I get a lick?
–Restaurant, St. Mark's Place
Overheard by: Eliza
Lady looking at another woman's Roman sandals: I don't like those Jesus-lookin' sandals!
–The Village
Girl: Do flats make your butt look big?
–9th St & 3rd Ave
Overheard by: Matt Morgan
Guy with faux-hawk: You know in Pee-wee's Big Adventure, after he loses his bike and everyone around him is riding bicycles? I feel that way with high-tops right now.
–14th & 1st
Overheard by: Heather
(trendy, skinny, Upper West Side woman on sidewalk is staring down at her feet and looking concerned)
Preppy 30-something boyfriend: I think your toes look better in those sandals.
–86th & Broadway
Overheard by: Sushene
Girl: My uncle is gay, like, flying-out-of-his-loafers gay.
–W 67th & Broadway
Overheard by: magical-newyork.blogspot.com
Female cop to two male cops: So he's standing there, really well dressed, nice shoes, and all of a sudden he pulls out this big, big (voice drops) boner, and says "Give me the shoes!"
–Continental Ave Station, Forest Hills
Prep school boy #1: I’m reading The Invisible Man, but I’m really disappointed.
Prep school boy #2: Really?
Prep school boy #1: Yeah, I mean, he’s not really invisible, you know?
Prep school boy #2: He’s not?
Prep school boy #1: No, he’s just black.
–96 Crosstown bus
Girl: I’m done with threesomes. Someone always gets hurt. It’s four-gies only from now on.
–Duane Reade, 32nd & Broadway
Overheard by: Jaina Wald
Man on cell: You got the what? The what? So you got the queen-sized bed!! You whore! You whore!
–Wall & Water
Overheard by: Aubrie
Man: Hey, anyone want to go to an orgy?
–Central Park
Loud teen boy: Dad, do we need condoms?
–Pharmacy, 82nd & Columbus
Girl on cell: Well it’s not even like anyone there had any real porn background!
–Union Square
Overheard by: Natalie
Guy on stoop: Dude! I did not give that girl VD.
–22nd & Broadway
Loud female suit: Well, at least he wasn’t sleeping with an intern!
–45th & Lex
Preppy girl on cell: Hey, girly, I got myself two tickets for us to go to the Dominican Republic for next week, and you know what that means: 7 days of Dominican cock. Yum!
–34th St
Overheard by: naidababy
Preppy girl: So, like, Salman Rushdie had to move to America because that guy issued this fatwa thing against him.
Hipster guy: You mean the Ayatollah?
Preppy girl: I think it’s pronounced “aya-toy-a.”
Hipster guy: Ummm…Yeah, if he were Spanish!
–Columbia University
Overheard by: not an Ivy-Leaguer
