Clothing

Old German man: Last night those people were staring at us. All of them, staring!
Old American woman: Yeah, they were. I wonder why.
Old German man: I bet they were German too, I wonder if they could tell I was German.
Old American woman: You were dressed pretty classy.

–LaGuardia Airport

Overheard by: Jake

Teen girl holding up lacy thong to friend: Yo! Anita! Get dis one!
Friend: Nah. I already got those! Remember? I wore them for those pictures.

–Strawberry, Union Square

Yuppie mom to crying daughter: Sophie, put your jacket on or you're going to get sick and have to get shots!
Detached father: Yeah, ten shots…and they'll hurt.

–Bleecker & MacDougal

Overheard by: Samskiii

Man: I'll give you the shirt off my back!
Woman: I don't want your shirt. I give you shirts! Why would I take it back?
(pause)
Man (singing): “We are the champions, we are the champions…”

–L Train

Overheard by: sweetchuck

Mom: Look at you! Why are your shoes so dirty? I told you that white sneakers were a bad idea…
Son: Whatever, saddlebags…
Mom: Excuse me?
Son: Let's be honest, mother. Those pants are not doing any justice to your hips.

–Central Park Zoo

Overheard by: Listening with amazement

Preppy guy: They say beggars can't be choosers, which makes sense, because we're choosers.

–Madison Square Park

Overheard by: Annie

Red Table change collector guy: Help feed the homeless of New York! All it takes is a penny and a heart, you fucking assholes.

–Times Square

Overheard by: Bemused

Girl to friend: I thought of you the other day; I saw a homeless man's penis.

–Lucky Jack's, Orchard St.

Overheard by: Argopelter

Horny dude (after being rejected by a girl at the bar): I asked her if she wanted a drink and she gave me the look that I give to homeless people on the subway.

–79th & Broadway

Guy to girl sitting at a sidewalk cafe: I know, what is with her? She dresses like a homeless person. And not Mary-Kate Olsen homeless but I-think-I-saw-her-passed-out-in-an-alleyway-with-a-heroin-needle-sticking-out-of-her-arm- homeless.

–10th St & 2nd Ave

Girl, to guy who has just spat on floor: Don't do that! Homeless people sleep there!

–6 Train Station

Teen girl to friend: You should get a t-shirt that says “Will work for chocolate.”
Friend: You should get a t-shirt that says “Will have sex for free”!

–Montegue & Henry

Overheard by: Hal

NYU freshman girl #1, crossing the street: My dad always says, “No! Don't cross the street yet!” and I'm always like, “Dad, I've lived here for two months, I think I know what I'm doing!”
NYU freshman girl #2: Ha ha! But you know, cab drivers are looking out for you.
NYU freshman girl #1: Yeah, that's their job. If they hit you, they get sued.
NYU freshman girl #2: Yeah. My shirt says it all. “NYU” pretty much means “you'll get sued.”

–23rd & 6th

Overheard by: EthanK

Well-endowed woman: Is this one of those fancy uplift bras?
Salesperson: Yes, ma'am, it is.
Well-endowed woman: All right, but if I get home and my titties still sag I'm gonna be mad at you!

–Victoria's Secret

Little kid: We're going to the city to get mommy titties!

–LIRR Train

Punk chick: This thing needs bazooms. I'm a punker chick with itty bitties.

–Midtown Office

Girl to female friend: Hey, did you know today is the three-year anniversary of my boobs?

–Union Square

Crazy lady trying to exchange a shirt: I can't go to work with my tits hanging out!

–Abercrombie & Fitch

Overheard by: me neither.

Chick on cell: In his defense, I forget about breasts, too.

–Columbia University

Overheard by: Wild Dog Boy