Clothing

Girlfriend: The last thing on the list is pantyhose.
Boyfriend: Pantyhose? I didn't know you wore pantyhose.
Girlfriend: I don't in the summer, because summer is the time to be free and relaxed, but now it's cold and I need to keep warm.
Boyfriend: If you are so free and relaxed in the summer, why are we having sex more now?
Girlfriend: Because now it's cold and I need to keep warm.

–Duane Reade

Teenager: Do you know where the Gay Pride Parade is?… I’m not gay!

–Astor Place

Guy: And so, this one gay guy in your office was wearing these pants, and his fly was open and this straight guy could see his penis, or some shit like that, right?

–9th St, Park Slope

Queer on cell: You really think she’s into gay guys?

–NYU

Guy, pointing to gay hipster: That’s like “I like it in the bum” written in hair.

–Peculier Pub, Bleecker St

Overheard by: Mad

Mom, to young son: It’s not a matter of being gay or not, darling. I just won’t let you participate in your school play.

–Broadway

Girl: Well, I couldn’t really sing the last part. We were both on our backs with our legs wide open. The only redeeming fact is that he was gay!

–Corbin Plaza, Brighton Beach

Overheard by: Anti-Traffic Girl

Flamboyant tween boy: I hate health class! You know what I’m going to do in health class today? I’m going to tell the teacher I’m gay! And that I like to suck dick!

–5th Ave, Park Slope

Comedy show ticket seller: Hey! You dropped your scarf!
(girl with scarf around her neck rolls eyes)
Comedy show ticket seller: Hey, you must live here!
Girl: Yeah, and I work in this fucking area, and you tell me that every single night when all I want to do is go home. (looks at tourists listening) Just so you know, “free comedy show” means two drink minimum, and the so-called comedians are just dumb asses who are not not funny at all.
Comedy show ticket seller: Woah! Marry me, please. I'm not trying to be funny, you are fucking amazing!
Girl: Fuck you.
Comedy show ticket seller to tourists: I'm being serious, she's the woman of my dreams!
Tourists: What?

–Times Square

Five-year-old boy: That shirt’s nice! Where you get it?
Five-year-old girl: The store!
Five-year-old boy, impressed: Damn!

–125th & St. Nicholas

Overheard by: Nicole

Mother: Honey, your dress is just too low. I know you don’t mean to, but when you wear things that show that much of you, you attract the wrong kind of men.
Scary Mexican man sitting across: Oh honey, you definitely do.
(girl hastily pulls her dress up)

–1 Train

Overheard by: Anna

Bimbette #1: So, I think I know what my problem is…
Bimbette #2: Oh, yeah? What’s that?
Bimbette #1: I think my underwear is on backwards.

–8th & 5th

Overheard by: Melissa Martinez

Chick #1: She got really upset with me for telling him that she got her wedding dress online.
Chick #2: Oh, I kind of understand that–
Chick #3, furiously: –What?! She can take his dick in her mouth, but she can’t tell him she got her wedding dress online?! She can put her face in his ass and not tell him she got her fucking dress online?!

–Pizza place near 5th Ave & DeGraw, Park Slope

Girl #1: I just wanted to scream at her to put on a goddamn bra and shave her fucking armpits!
Girl #2: Oh my god, I know. I mean, it’s not like she has much there… But it’s something and you gotta cover those puppies up.

–Greenwich Village

Headline by: RaRa

Runners-Up:
· “And the Way She Was Holding Baby Jesus–ROTFL” – ddv
· “I Mean, You’d Think She’d WANT to Look Good at Her Own Communion!” – RaRa
· “Joan and Melissa Rivers’ Commentary at the Bronx Zoo” – allison
· “Or Carry Them in a Bag Like a Celebrity” – Andrew
· “Where Have All the Paula Cole’s Gone?” – chubba
· “Yeah, But Jagged Little Pill Was Such a Great Album” – blistexaddict
· “You’d Think by the Age Of 8, She’d Get That!” – MalG

Click here to see the new Headline Contest

Girl to friend in a mini skirt with her legs open: Katie, close your legs!
Lethargic friend: I don’t care. I am wearing two pairs of tights and granny panties.

–Silver Center, NYU

Overheard by: AJ

Teacher: What's used to cover a beast?
Student: Underwear?

–Francis Lewis High School

Overheard by: Thank God I'm Not The Beast.