Guys

Wednesday Feel Trapped in a One-Liner's Body

Ghetto lady to another: Her son is a lesbian!

–Port Authority Bus Station

Suit to friend: Did I ever tell you about the time I ran into a Dunkin Donuts Drive Thru window with a transvestite in my back seat?

–N Train

Overheard by: Tater

Cop: The trannies hate the DVDs. They just can't get along. They hate each other more than the Bloods and the Crips!

–Union Square

Overheard by: Jon A.

Girl on cell: He just turned around and slipped into the skirt, and I just had to tell him! (pause) No, it didn't flatter his figure.

–Avery Fisher Hall, Lincoln Center

Crazy guy, pointing to girl sitting on fireplug: She's a man! That girl's a man! She's a man! Heh, heh…okay, stay there, I'll be right back. (pause) To punch you in the face!

–23rd & 7th

Overheard by: EthanK

Guy on phone: First you wanted to be a car salesman, and now you want to be drag queen?

–31st b/w 9th &10th

Overheard by: roommate of guy on phone

Though I Guess I Should Stop Referring to Jersey That Way

Guy: Excuse me miss, do you know what time it is?
Girl: Uh… (checks phone) 10:06.
Guy: Thanks, I don't have a phone yet, I just got out of prison.

–Penn Station

Overheard by: Megan in the Netherlands

Don't Forget to Bite My Junk!

Preppy white guy: I'm sorry, but you can't.
Hippie white chick: Bite my junk, bitch!
Preppy white guy, sighing: Okay, I'll see you at dinner.
Hippie white chick: Later! Love you!

–Henry St & Atlantic Ave, Brooklyn Heights

And the Fact That They're Douchebags Creates Lubrication

Dude in crowded subway car, to friend he's showing around town: That's why hipsters are all so thin, so they can move easily through trains.
Friend: So, is that, like, a requirement here?
Dude: Yeah, there's a practical reason for it.

–R Train

Overheard by: Morning Glory

A Real New Yorker Would Just Do It.

Guy shoving himself onto a full train: Maybe if y'all moved a little I would fit!
Incredibly irate guy being shoved: Maybe if I punch you in the fucking face you'll get off this train so the doors will close!

–Penn Station

Overheard by: McJensen

And I Do Mean “Up”

Girl, as UPS truck passes: Would you rather call FedEx or UPS?
Guy: I don't mind, as long as my package gets to where it needs to be.
Girl: Where does your package need to go?
Guy: My package needs to go up in your sister in Virgina.

–Time Square

Dennis the Menace Grew Up Pretty Much As Expected

MTA worker: Buy a ticket.
Guy banging on turnstile: Nooooo.
MTA worker: Buy a ticket.
Guy while diving under turnstile: No! Fuck you!

–SoHo

Remember When I Borrowed Your Sleeping Bag?

Guy #1: Yeah, I can remember a bunch of times I've shit myself.
Guy #2: Yeah?
Guy #1: Yeah, I think I can remember all the way back to one time when I was like three.
Guy #2: Oh, man. I can remember a time like last year.

–84th St & York

Ten Bucks Says They End Up in the Bathroom Making Out

Uptight, Greg-type dude: Doesn't it hurt to sit with your legs like that?
Cheerful, Dharma-type chick, in lotus position on bar stool: Nope!
Uptight, Greg-type dude, after short pause: I shall pray for you, my dear.

–St. Mark's Ale House, St. Mark's Place

Overheard by: Amber Star

…So You Can Be Divorced by at Least Thirty.

Drunk guy: If I'm not married by the time I'm twenty-five or twenty-six…
Drunk girl: You haaaaave to be married by the time you're twenty-five.

–Lower East Side

Overheard by: very single twenty-five year old. ouch.

© 2026 OverheardinNewYork.com
Hat Tip 🎩 to The Marketing Scientist