Upper East Side

Tourista #1, about street sign with large bend in middle: Why does the Gershwin Way sign have a curve in it like that?
Tourista #2: I think it’s to symbolize Gershwin’s music.
New Yorker passerby: A truck backed into it, ya stupid bitches.

–NW corner, E 50 St & Broadway

Overheard by: Big Larry

JAP halting mid-stride: Wait a sec… Why are my pants wet?!

–82nd & 2nd

Overheard by: my boyfriend is a grizzly bear

Headline by: John

Runners-Up:
· “And Who Dropped That Baby?” – trade800
· “Bob the Urinating Hobo Ninja Strikes Again” – Darryl S.
· “Did A Bag Of Money Just Walk By?” – Jolly
· “The Joys Of Unknown Pregnancy Coming Full Term” – The Lazy Canadian
· “This Eventually Happens to Every New Yorker” – Dagre
· “Was Too Busy Shopping to Be Toilet Trained” – G

Click here to see the new Headline Contest

Student, looking at clock: It’s time to go, Mr. T.
Teacher, slowly and loudly: It’s time for you to die.

–E 68th St

Stoner: She did coke, like, six times last week and was bleeding out of her nose.
Black girl: Ahhh, I love her.

–82nd & 2nd

Overheard by: yoni

Dude #1: Dude, that girl is looking at you like a fat girl looks at cake.
Dude #2: She is a fat girl.
Dude #1: Fine. She is looking at you like you are cake.

–UES

Smoker girl: We should do a wine power-hour tonight.
Friend: A wine power-hour is a bad idea. I lost my virginity after a wine power-ten minutes.

–83rd & 1st

Overheard by: M.J.

11-year-old boy smiling mischievously: Mom, I’ve been desiring a lot lately.
Frazzled UES mom: Would you please stop doing that?

–80th & York

Overheard by: Nicole

Bimbette #1: I got the hottest shoes. They’re like Burberry, but cuter, with sexy heels. Zimbabwe likes them.
Bimbette #2: His name is Zimbabwe?
Bimbette #1: Well, no one can pronounce it. It starts with a ‘K,’ but I think it sounds retarded, so I’d rather call him Zimbabwe.

–66th & 3rd

Hardhat #1 with pavement-smoothing machine: It won’t start.
Hardhat #2: I tell ya, if it’s got tits or wheels, it’s gonna give ya problems.

–75th & 3rd

Overheard by: Mo

Stoner #1: We’re married now.
Hoochie: We are?
Stoner #1: Yeah. We just met a sea captain, and he married us.
Stoner #2: Oh, Ahab?

–89th & York