Questions

Old man: Hah! I fell asleep at her funeral!

–3rd Ave, b/w 10th & 11th

Overheard by: j

Man to woman: Hey you! You were in my dream last night. You, myself and a bunch of people in the office were having an orgy on a mattress right in front of our office. At first it was great, but then it became awkward because people kept walking into the office and we got in their way.

–34th St & 6th Ave

Man with French accent on cell: Do we have room for her, or will she have to sleep in the dungeon?

–32nd & Broadway

Overheard by: LC

(guy is woken up by a friend after falling asleep on the train)
Guy: You dude, why you wake me up! I was having the best dream. There was shorties everywhere. There was shorties in trees and shit!

–2 Train

Conductor: For all of you running late, we are being delayed by another train with the emergency break on. Or you could tell ’em you just slept in today.

–D Train

Overheard by: blistexaddict

Patron: Do these stairs go up?

–Metropolitan Museum of Art

Overheard by: Maura

Drunk White Sox fan to passerby: Hey, what time does Times Square close?

–Outside Yankee Stadium

Overheard by: giovanna

Dude at the next table: Is Long Island really an island?

–Peter Luger’s, Williamsburg

Overheard by: Yes, he really just said that

(girl sees poster for Army Wives and turns to friend)
Girl: I don’t get that show. Are they married to army dudes or something?

–C Train

Southern lady: Empire State ReBuilding? Does that mean they’re moving it?

–33rd & 5th

Overheard by: Katie Mainc

Little boy to mother: Mom, have you ever heard of Anne Frank?
(silence)
Little boy: You know, she was this holocaust victim who lived in an attic and wrote this diary?
(pause)
Mother: I mean, I’ve read about the holocaust, but I don’t know any specific authors.

–Smith & Sackett, Carroll Gardens

Overheard by: David

Little boy looking at photos being sold on street: Why do they call it Gay Street?
Dad: They got all kinds of fucked up names for streets in this city.

–Times Square

Overheard by: R

Bar guy #1: Hey, how’s it going? How’s your brother?
Bar guy #2: He had brain surgery today.

–W 158th & Broadway

Overheard by: puppy

(goth chick runs down the street shrieking, followed by her hipster-chick friend with tiger face paint)
Young black girl #1: What’s happening?
Young black girl #2: Yeah, what’s with all the crazy white people?

–St Marks & 3rd Ave

Overheard by: Tigertail

Headline by: chrissmari

Runners-Up:
· “How Young Oprah Got the Idea for Her Show” – Doug
· “Let’s Go Back to Harlem Where It’s Safe” – Caitlin
· “Obama Better Fix That Shit His First Day” – Steve J
· “The Little-Known Eighth Sign Of the Apocalypse” – samson
· “Wait Until You Meet Dennis Rodman” – Aussie_Girl

Click here to see the new Headline Contest

Hipster #1: Why don’t they make cat cheese? You can milk anything with nipples.
Hipster #2: Why don’t they make Robert De Niro cheese?

–Franklin Avenue Shuttle

(two girls standing in line)
Girl #1(with two cupcakes): I can justify buying two because I walk here and walk home.
Girl #2: Are you walking home tonight?
Girl #3: No.

–Magnolia Bakery

Tall scraggle-tooth guy with eye patch, in hoarse creepy voice: Do you like balloon animals? I like balloon animals!
Startled passerby: What the fuck ass hell?

–6th Ave & W 8th St

Overheard by: Rose Fox

(crazy woman talking to self)
Guy sitting next to her: Sorry, did you say something?
Crazy woman: No, I have an ear piercing.
Guy: Oh, in the other ear?
Crazy woman: No, this one (points to the ear closest to him). It’s all the way inside my ear. It’s Australian.

–Jane St & Greenwich Ave