Beauty

Nine-year-old blonde: I’m not pretty.
Nine-year-old brunette: Yes, you are. You’re super pretty!
Nine-year-old blonde: I’m not pretty enough. I’m not Paris Hilton-pretty.

–Hudson & Perry

Overheard by: Talia

Dude: You really don’t look much like your picture.
Girl: Is that a good thing or a bad thing?
Dude: I’m still deciding.

–W 3rd & Sullivan

Overheard by: jor

Teen girl #1: I hate riding in her car.
Teen girl #2: I know! It smells like dog, and then you look like dog.

–Bushwick

Overheard by: -|

Eager, straight-ish hipster dude to posse: We could ask gay guys which one of us they think is cuter…
Cute hipster friend: No, I always win that game.

–Pyramid, Ave A, between 6th & 7th St

Overheard by: Dan

Doctor #1, about Norah Jones: Did you know her father is Ravi Shankar?
Doctor #2: Her mother must be extremely good-looking.

–Doctors’ lounge, St. Vincent’s Hospital

Overheard by: Danny D

Headline by: s h

Runners-Up:

· “And we know why she didn’t come.” – Offbalance

· “Nip, Tuck, or Genetic Luck?” – Iconny

· “Or Maybe It’s Just that When You Multiply a Negative by a Negative, You End Up With a Positive” – Vasyl

· “Sex and the Sitar” – nicky c

· “The Good, the Bad, and the Ravi” – Riley


Click here to see the new Headline Contest

Rider #1: Damn, this bike seat is uncomfortable.
Rider #2: Damn, that VS model is hot.
Rider #1: Shit, my yoddle feels like it’s skewered like a lamb chop.
Rider #2: I wonder if she’ll agree to be my next wife…

–42nd & 6th

Chick: She has low self-esteem.
Dude: She should. She’s mad ugly.
Chick: I’ve known people who are ugly but really beautiful.
Dude: No.
Chick: No, really! I’ve seen ugly men with beautiful women and ugly women with handsome men.
Dude: I’m dumb-shallow. If you don’t look good, you can’t be my friend.
Chick: But you’re judging people. Like God.
Dude: Fuck that. I pay my own rent. I don’t need anybody. I’m straight, but all my guy friends look good. If you’re ugly, you can’t be my friend. I’m dumb-shallow. [A few minutes later] Yo, if someone says I don’t look good, somethin’s wrong with them or their eyes, ’cause I look good.

–4 train, rush hour

Overheard by: Veej

WASP #1: You look so tan!
WASP #2: Oh, no, it’s actually just high blood pressure.
WASP #3: Well, it sure suits you!

–Armory Show

Overheard by: Elizabeth

Woman, about Kate Moss photo: At the time they don’t think that you’re on drugs, they just think that you’re beautiful.

–Brooklyn Museum

Overheard by: Harried Visitor

Old woman to another: He had a beautiful, beautiful body, a handsome face, and a big old dick that would just kill ya!

–14th & Broadway

Overheard by: rita

Perfume seller: Designer perfume! Five dollars. Only five dollars. Discounts for pretty ladies. [Looks at lady passerby] For you… $4.99.

–Penn Station

Overheard by: Renea

Guy to chick with him: I’d hold your hand, but my heart hates uggoes.

–67th & 1st

Girl watching two hot Mormon guys walk by: I think it evens out. I have actually seen ugly Mormons.

–Flatbush & 5th Ave, Brooklyn

Overheard by: stephanie k

Dude: Yeah, she’s not ugly, but she’s definitely not pretty. But she wants me to set her up with one of my friends. I told her that they’re all either married or ugly, but then I realized I should set her up with one of the uglies because it’ll help her self esteem.

–Rangers Game, Madison Square Garden

Overheard by: Veronica

Hoochie: I mean, he’s not the ugliest guy I’ve made out with. I made out with a guy who looked like Alf.

–Time Warner Center

Overheard by: Tater Tot

Old guy: I’m a good judge of character. That’s why I never talk to her. That and because she’s got a face like a foot. I never talk to ugly people.

–Viacom elevator, 1515 Broadway