Preppies

Six-year-old hippie girl to babysitter: If it’s okay with you, can you take Tommy and I to Grey Dog, please?
Six-year-old preppy boy: What’s “Grey Dog”?
Six-year-old hippie girl: My favorite coffee shop.

–Bleecker & 6th Ave

Headline by: chubba

Runners-Up:
· “By the Time She Was 13 She Had a Favorite Abortion Clinic.” – DR G LUV
· “I Just Get The Cafe Au Breast Milk.” – cbeck
· “If It Was 1908, She’d Be Working in a Textile Factory” – Nate
· “The Lattes Come with Biodegradable Crazy Straws” – Kristen
· “Their Mom Had Caffinated Breast Milk” – Josh

Click here to see the new Headline Contest

Preppy girl #1: Eek! No humping. Stop!
Preppy girl #2, pressing her thighs against #1: Not even side humping?
Preppy girl #1: No, not here… [Winks.]

–75th & Broadway

Overheard by: A Queens Librarian/ Rockstar

Preppy teen girl #1: … And there was blood, like, everywhere!
Preppy teen girl #2: Haha, oh my god.

–Soho

Overheard by: dannyl

Conductor: You know what stop this is?
Alabaster college prep: Harlem?
Conductor: Mmm-hm… Hope you find what you’re looking for, son.

–125th St station, Harlem

Preppy guy #1: I just don’t see myself getting married anymore.
Preppy guy #2: Yeah, I’ve totally lost the will to live.
Preppy guy #1: You’ve lost the will to live?!
Preppy guy #2: What? No, I meant to say I’ve lost the will to get married… Okay, I’ve lost the will to live.

–Wall St

Preppy girl: I don’t get it. How are you too busy to have sex but have enough time to get head?
Thug: Well, I don’t have to do any work. All I have to do is lie there.
Preppy girl: Oh, okay. What time should I come over?

–Ferry to Ellis Island

15-year-old preppy #1: I think Lisa’s really cool. We should hang out with her more.
15-year-old preppy #2 Yeah, she seems like a really cool girl. I guess her boyfriend’s in jail or something… And she has his name tattooed on her clit [gestures to stomach area] or something…

–Atlantic Ave

Preppy girl #1: Are these boyfriend panties, or are these cheating-on-your-boyfriend panties?
Preppy girl #2: I think they’re a little slutty.
Preppy girl #1: So, for cheating?
Preppy girl #2: Yeah.
Preppy girl #1: Do you think this is all they have, or is there another drawer?

–Victoria’s Secret

Preppy girl to friend: I vote to ban fat people from trains. [Woman nearby throws angry look.] Just at rush hour! [Woman mutters under her breath.] Local-only chub train?

–Crowded 3 train

Hobo: The government just doesn’t understand the power of my feet!
Preppy guy: I see. Go on…

–70th & Columbus