Clothing

Customer: I’d like to return this shirt. It fits me just right, but the tag says ‘Large,’ and I don’t wear a size Large.
Returns person: Okay, no problem.

–H&M, 34th & 7th

Overheard by: Andrea Reese

UES trophy wife #1, in black dress: … And the dress was only twenty-six hundred dollars!
UES trophy wife #2: Wow, that’s fabulous!

–David Burke & Donatella Restaurant

Lady suit: Do you know what your skirt is doing?
NYU student: Is it blowing up again?
Lady suit: Yes. Everyone can see your entire ass.
NYU student: You love it.
Lady suit, snorting: Not really.

–12th & 3rd

Overheard by: Jenna

Dad: If you want to be a cross dresser, I’m totally okay with that.
Son: Nice!

–Bloomingdale’s, 59th St

Overheard by: Bri

Male attorney: You’re wearing a dress? But you have to be in court today!
Female attorney: With as much respect as I have for the New York City supreme court judges, they’re lucky I’m wearing a dress. I should be wearing a… a… a bikini.

–Law office, Midtown

FedEx guy to passerby: Hey, they’re my trousers! What are you doing wearing my fuckin’ trousers?!

–Houston & 1st

Man with water-cooler jug of coins: Please give to help the homeless. Anything can help… A smile, a pork chop, a pair of pants…

–55th & 5th

Jersey hoochie walks by, her thong showing conspicuously.

Matter-of-fact mom to eight-year-old son: That girl’s going to lose her pants.

–NJ Transit terminal, Penn Station

Overheard by: cockrin

Guy on phone: … And so I put my hands in his pants and realized, ‘Oh my god, I’m gay!’

–McDonald’s, Times Square

Little boy to mother: These pants are too small! I’m gonna get a yeast infection if I put these on!

–Target

Overheard by: The dressing room next door

Charity worker: Help the homeless! [Androgynous person walks by] Even a pretty girl… boy… whatever-that-was can help!

–Times Square

Chick, wistfully: That was Vadim. He was from St. Petersburg. When we broke up he stole all my dresses.

–A train

Overheard by: Rose Fox

Large black security guard, inspecting guy’s Sephora bag: You da man!

–Hayden Planetarium

Pierced 20-ish chick: So, the last time I pegged a guy he wouldn’t stop jabbering on and on about how much he loved trannies. It just made me shove in the strap-on harder.

–Delancey & Orchard

Overheard by: Californian

Guy: I sirred a ma’am today. But, in my defense, she was a very sir-able ma’am.

–33rd & Broadway

Old lady with dog in stroller: I’ve met you before.
Old lady with three dogs on a leash: Oh, really? Where?
Old lady with dog in stroller: You were at the nail shop. You asked me about my unitard.

–Christopher & Bleecker

Older drunk, tightly hugging young guy: … And don’t think I’m gonna forget. When that happened, who gave me new underwears and washed my ass?
Younger guy, trying to get away: Man, just forget about that!
Older drunk: No! I’m not gonna forget about that!

–Greenpoint, Brooklyn

Asian queer, looking over his shoulder: I think I jerked him off.
Italian queer: Who?
Asian queer: That guy in the green shirt… It’s pretty bad when you can’t keep track of all the people you’ve jerked off.

–Union Square