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
Preppy guy #1: Oh, man, I can’t believe you. You’re just such a… a gay cowboy.
Preppy guy #2: Haha, Brian’s* not a cowboy.
Brian*: Oh, thanks, dude. Thanks.
–Macy’s
Overheard by: greg
Preppy girl to honking SUV driver: Fuck you!
Asian guy, walking other way: Bless you!
–59th & Park
Overheard by: Just trying to cross the street
Preppy guy #1: I hate geese shit on fields.
Preppy guy #2: It’s not so bad. It’s a good lubricant for when you slide-tackle people. You know, you just keep sliding…
Preppy guy #3: Dude, I can’t remember the last time I jerked off using geese shit. It can’t be that good a lubricant!
–Central Park
Guy #1: I think I’d come in third.
Guy #2: Why third? Why not first or second?
Guy #1: I don’t know, I probably don’t have the biggest, but it isn’t the smallest either, so I figured third.
Guy #3: Wait, then whose dick do you think is the smallest?
Guy #1: I don’t fucking know! I just don’t think I have the smallest, so I’m sure I beat one of you motherfuckers.
Guy #4: Dude, sounds like you got a small dick.
–24th & Lexington
Overheard by: paul10003
