Clothing

Teenage nymphette: I want to go back to the hotel and go swimming.
Chaperone: What do you have to swim in?
Teenage nymphette: My bra and thong.
Chaperone: Oh no no, I don’t think so.

–Top of the Rock Observation Floor

Hobo with two jars in front of him: Food or drugs! Choose whether you’d like to sponsor my evening shot or dinner!

–Central Park

Homeless man: Hey, bindi-a, lookin’ good today! (Indian girl ignores his comment, begins to walk away). Fine! When you get mugged, I’m not helping you!

–Washington Square Park

Enterprising lady hobo: You could use your credit card to get cash, and give me the cash.

–Outside Dunkin’ Donuts, Brooklyn

Overheard by: Rich Mintz

Panhandling hobo: Spare some change for a large bottle of water and a nice Chef salad? Spare some change for bottled water and salad?

–Broadway & 10th St

Hobo: Hey lemme borrow those red Converse! I’ve got a hot date with Monica Lewinsky tonight!

–14th & 6th

Hobo to another: "You’re gonna turn me into a waffle?" That’s what she told me, you said! A waffle? Oh no, I don’t think so!

–23rd b/w 6th & 7th

Overheard by: sara

Crazy hobo: Watch out for traffic and knuckleheads! Beware! (points at random pedestrian) Him! He’s a knucklehead! Don’t trust him!

–5th Ave & 49th St

Dude #1: Today, I saw someone wearing jeans that were like, way too tight.
Asian chick: Skinny jeans? I love skinny jeans!
Dude #1: On a guy? These were on a guy!
Asian chick: Oh, then… no.
Dude #1: Guys shouldn’t wear their jeans that tight. It’s bad for the balls.
Dude #2: It’s seriously bad for the balls. It’s unhealthy.
Asian chick (skeptically): Nuh-uh.
Dude #2: You wouldn’t know!
Dude #1: You don’t even have balls!
Asian chick: No. (considers) But if I did, I’d play with them all the time.

–NYU Elevator

Overheard by: Hannah

Girl #1: So both the girls took off their panties and spread their cheeks for the crowd. And you would not believe it, but the one girl started eating the other one’s ass!
Girl #2: Nothing says “goodnight” like a good ass licking.

–Vespa, Upper East Side

Overheard by: Steve

Bum #1, slurring: Hey! That’s a nice shirt you got!
Bum #2, walking across the crosswalk, also slurring: You look like a catfish! [Turns to guy in a car.] Doesn’t he look like a damn catfish!?

–12th St & 8th Ave

Daughter: This is a really nice dress for my first wedding, no?
Mother: Well, for the next one you will have more money, so you can get something even nicer.

–77th & Madison

Bearded guy to female friend: I went to Williamsburg and was like: "Who *are* all these people that look just like me?

–Café Pick Me Up, 9th & Ave A

Overheard by: Doibles

Young hipster: I only date girls from the Lower East Side or Williamsburg.

–9th St & Ave A

Overheard by: bildita

NYU girl to friend: Berlin is like, the new, like… Williamsburg.

–4th Ave & 12th St

Overheard by: john.ainley

Young girl: I’m Middle Eastern, and I swear to god if I see another honky wearing a keffiyeh I’m going to commit fucking Jihad on Williamsburg.

–Park Slope, Brooklyn

Visitor, looking around in bewilderment: Why is everyone trying to look like they’re poor?

–Bagel Shop, Williamsburg

Overheard by: NCT

Preppy girl: Come on, you have to go with us.
Athletic girl: I can’t, remember I don’t have a bra on and I have Lynn’s shirt.

–Cafeteria, Queens College

Overheard by: Waiting for time to pass.

Woman in stall #1: I hate it when this happens!
Woman in stall #2: What?
Woman in stall #1: These pants! They looked so nice but they flatten my ass. My ass is flat now. I look like pancake ass!

–Fitting Room, Staten Island

Guy #1: Yo, man. I lost seven pounds. Can you believe it?
Guy #2: Oh yeah? Really?
Guy #1: Yeah, I got a fuckin’ shoestring on my pants.
Guy #2: Uh…
Guy #1: I don’t like this. I liked being fat.

–CVS, Allerton

Overheard by: Lee