Questions

Jon Lovitz, Is That You Again?

Girl #1: Oh my gosh. I have to pee so bad. Do you think this restaurant will let me use their bathroom?
Girl #2: I don't know, why don't you ask?
Hobo, sunbathing in front of restaurant: Why, of course you may use the bathroom, young lady. But you will have to pay $5.
Girl #1: How do you know?
Hobo: Because this is my restaurant and I own this building.
Girl #2: I find that hard to believe.
Hobo: Look, you can believe me or not, but if you don't pay me the $5 fee, I'm going to expose my golden privates to you. Either way, I come out on top, you see?
Girl #2: Unbelievable! (walks away)
Hobo: Why, thank you.

–Times Square

That, or a Botched Suicide Attempt

Middle aged woman: When you hear him say that, you just grab some cake and ice cream.
Younger woman: Why?
Middle aged woman: Because that means he just dumped you…and you'll need to gain some weight to make him feel like asshole.

–Central Park

And by That I Mean, “Why Do You Hate Freedom?”

Guy #1: I told the manager they need to start recycling.
Guy #2: Why?
Guy #1: Cuz they don't recycle.
Guy #2: So what!?

–41st & 7th

There Are No Small Wednesdays– Only Small One-Liners.

Girl on cell, defiantly: Listen, I can keep my midget in your closet whenever I damn please!

–72nd & Columbus

Man handing out cards to random passers-by: They have midget strippers, buddy, and you can bring your guitar!

–42nd & 7th

Overheard by: Katy

Guy, to friend: You can't call yourself a grown man if you sit down and your feet dangle off the chair.

–Victoria's Secret

Overheard by: Emm

Black guy pushing cart: Man, I miss my two-headed midget friend… He was my best man.

–Union Square

Woman on cell: Have I been an angry little munchkin?

–Whole Foods, Union Square

Overheard by: TheMac

A Gay Man Told Her about “Killer Shorts”

Blonde: So, where’d y’all go on vacation?
Brunette: Bermuda.
Blonde: And y’all came back alive?!

–Union Square

Wednesday Pick-Up-Liners

Guy, bumping into girlfriend as bus lurches: Sorry baby, that’s gravity. I can’t help it, I’m physically attracted to you.

–M116 Bus

Overheard by: I hate the bus

Construction worker hitting on young girl: Hey baby, you are too cute to be so pretty!

–Allen & East Houston

Black bag seller to passerby: Hey sweetheart, you wanna buy a bag today? I’ll tell you what, you buy a bag and I’ll give you my number for free.

–33rd & Broadway

Man to teenage girls: Do you and your friends like to wrestle? I swear to god I could take you all.

–Times Square

Overheard by: yearbookie

Homie to friends: They say in the old days you couldn’t even holler at a woman cause she wouldn’t answer you.

–South Williamsburg

Overheard by: DanielXY

Homeless man to cute passerby: Nice knees.

–Central Park

Ooh, Awkward for Somebody, Huh?

Doctor #1: Who's taking care of [name of patient]?
Doctor #2: Not me, why?
Doctor #1: Nothing really, just that he's dead.

–Hospital, Manhattan

Overheard by: Lorenzo

Oh My!

Kid: What's a safari?
Young mom: It's a trip you can take in Africa where you can see animals like lions and tigers, and… bears.

–Central Park Zoo

Overheard by: kinicke

What? I Read Lips.

Drunk ass guy #1: (mumbles something drunk)
Drunk ass guy #2: What?
Drunk ass guy #1: (mumbles something drunk again)
Drunk ass guy #2: I can't hear you…I have a lazy eye!

–Gym Bar, Chelsea

Did You Skip Sex Education?

Hipster #1: Why are there so many pregnant women? I don't get it.
Hipster #2: Well, nine months ago was winter. When there's a blizzard, nine months later there's just babies everywhere.

–Penn Station

Overheard by: o!valencia

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