Clothing

Professor: Gods, these students. It’s like they just don’t get it, you tell them things and two minutes later they ask you the same thing. How did they get here? What are they going to major in? In "homelessness"?

–English Department, Hostos Community College

Well-dressed 20-something girl: Homeless people tell me to cheer up all the time!

–1 train

Rich woman #1, fixing rich woman #2’s scarf: [laughs] Oh my god, you look homeless!

–1 Train

Overheard by: sagehen

Well-dressed woman on cell: It’s just another Wednesday and I’m a bag lady.

–Columbia University

Overheard by: Ladle

Mother to her flock of children entering the train and then getting off: Run guys run, theres a homeless guy on that train! Run!

–F Train

Overheard by: yana

Young black teen: Is that a North Face jacket you're wearing?
White guy: Yes, it is.
Other young black teen: Do you use it to go skiing?
White guy: Uh, yes.
Young black teen to friend: See! I told you white people use North Face jackets to go skiing!

–F Train

Hipster girl #1: Oh my god! Did you see her shorts?
Hipster girl #2: Oh, I know. She might as well be fucking a black guy right here on the street corner.

–54th & 2nd

Overheard by: girl in shorts’ friend

Tourist lady #1: Oh, it’s worth paying the cab fare. I mean, the subway…well, after September 11th it’s just not safe, you know?
Tourist lady #2: You’ve ridden the subway before?
Tourist lady #1: No, it smells weird.

–Hunt Valley bus

Overheard by: Katie Cheek

Prospective girl #1: OK, so tomorrow, let’s all wear our “I Heart NY” t-shirts.
Prospective girl #2: Yeah! And I can wear my Columbia sweatshirt over it!

–Morningside Heights

Toddler: Why is Jack-Jack’s name “Jack-Jack”? Why not regular Jack?
Mom: That’s just a nickname. I think his real name is just plain Jack.
Toddler: Can my nickname be Johann-Johann?

–1 train

Overheard by: Matt G

Hispanic teen #1: Yo, man, I was with this girl last night, and she was dressed all naked and shit, man.
Hispanic teen #2: Word? She was dressed all naked?
Hispanic teen #1: [Nods.]Hispanic teen #3: Word?

–Houston & Washington

Drunk girl: Can you put my phone in your pocket?
Friend: But your pants have pockets!
Drunk girl: No, they don’t! That’s just a glitch in the matrix!

–2 train

Tourist #1: Last night I wasn’t really wild. I really want to be wild tonight.
Tourist #2: Last night you weren’t wild? I would actually be a little scared to see you go really wild, then.
Tourist #1: Well tonight I’m going to be really crazy. Tonight I’m going to wear my yellow dress!

–Eugene O’Neill Theatre

Cop on cell: Yeah, Adam just called. Are there bodies there?

–Outside Times Square Police Station

Overheard by: leah

Police officer on crowd control duty: If you was special, you'd get on the sidewalk. If you was my family, you'd get on the sidewalk.

–45th & Broadway

Overheard by: Claire

Little boy to mother, after policeman walks by: Mom, it's the five-o!

–38th St, Astoria

Man: Yo, I was so twisted last night. I was in the cop car and he was like, "no drinking in the cop car!"

–Lexington & 75th

Overheard by: wb

Cop to victim: So the doors and windows were locked,no sign of forced entry…and you're sure that your panty drawer was rifled through and unknown items are missing?

–Bensonhurst

Drunk girl: I'm unzipped and unbuttoned.
Passer by: Ready to go!

–Rubulad, Brooklyn

Headline by: unzipped, but buttoned.

Runners-Up:
· “…To the Bathroom!” – CherryPie
· “…To the STD Clinic” – JuzouShades
· “And Just Like That, Debbie Does New York Was Well on Its Way” – Buck Neked
· “Thunder! Thunder! HO!!!!” – John
· “Why Work for Sex When You Can Grab Low Hanging Fruit?” – the evan

Click here to see the new Headline Contest

Bimbo: I’d put on a sweater and baggy pants, and everyone would be like, “Wow, that’s so Margello!”

–Ave A & 3rd St.