Clothing

Asian girl: Your hair was so soft when you were a baby, I couldn't put a shirt on you because it would slip off.
Little sister: Haha! (pause) I don't get it.

–R Train

Disheveled gentleman: Hey, man, can you spare some change? I need a bottle of vodka, a bag of marijuana, and a prostitute. I'm desperate!

–East Village

Overheard by: Matty Mac

Toothless lady on street corner to friend: I ain't never been to jail, I ain't never fucked nobody for money!

–Brooklyn

Older Guido to young hipster: And then you got a fuckin' hooker on your hand, what are you going to to do?

–Mulberry

Overheard by: nina

Clean-cut queer: So she says "where are you going after this?" and I say "I think I'm just going to go back to the hotel and get some sleep" and she says "do you want company?" and I say "well, you're not really my type" and she says "I've got lots of friends… What's your type?" and I say "boys." And she's all, "oh, well, that's nice!" And then she leaves pretty quickly. And my friend says "who was that? Do you know her?" and I say, "no, she's just some very, very, very friendly girl. In a gold lamé cocktail dress. On a Tuesday night."

–6 Train

Overheard by: Rose Fox

Guy on cell: I wish I was in Florida–the hookers down there owe me 8 bucks and a beer!

–Astoria

Chubby girl: Hi, your top is gorgeous! Where'd you get it?
Skinny girl: Um, Greece.
Chubby girl: Well, aren't you special?

–Union Square

Hipster girl to friend: I told her it was the wrong kind of plaid. Not all flannels are equal.

–Bowery & Bleecker

Overheard by: but lumberjacks are supposed to be burly men!

Hipster to another: And I was like "Do you want some nail polish for that camel toe?"

–2nd Ave

Overheard by: Shan

Hipster guy singing to self in country twang: Whennnn am I gonna get me sommmme Ugg boooooots?

–4th Ave & 13th St

Hipster guy in eyeliner and mascara: I was being facetious… I would not wear leggings.

–Jamba Juice, 13th St & University

Overheard by: helenathegreat

Hipster girl screaming on cell: I want you to want me to want to touch you!

–Columbus Circle

Fat suit during movie, about fur coat on screen: Do you want one of those?
Girl half his age: No, I don't really like fur.

–Regal Cinema 14

Overheard by: Mark

Exhausted woman with backpack: Why do I have to be so fat?

–42nd St

Gossip Girl clone to another: Oh my god! Can you even imagine being obese in this weather?

–Lafayette & Spring

Skinny gangster white boy: Yo, dude, are we hanging out with those fat chicks?

–96th St & Lexington

Overheard by: great standards

Chubby girl yelling on cell: Yeah, and her bridesmaid dress totally accentuates my back fat–as if I didn't have enough problems!

–47th & 3rd

Girl: Oh, lets go to Prada!
Guy: I hate Prada! Prada means not eating for a month!

–Outside Prada Store, SoHo

Guy dressed only in tighty whiteys to bartender: I know I'm only wearing underwear, but can you please turn up the air conditioning?
Bartender: Yeah.
Guy dressed only in tighty whiteys: I'm speaking on behalf of several people. Well, other people who might come in here in their underwear.

–The Ritz, Hell's Kitchen

Girl in truly ridiculous dress: I am a strong, independent woman! I don't need a man in my life!
Friend: Amy*, you're wearing pink and ruffles.

–Lincoln Center

JAP #1: It's like seeing a midget in drag.
JAP #2: Oh, I've always wanted to see that.

–35th St & Lexington