Physical appearance

Preppy guy: They say beggars can't be choosers, which makes sense, because we're choosers.

–Madison Square Park

Overheard by: Annie

Red Table change collector guy: Help feed the homeless of New York! All it takes is a penny and a heart, you fucking assholes.

–Times Square

Overheard by: Bemused

Girl to friend: I thought of you the other day; I saw a homeless man's penis.

–Lucky Jack's, Orchard St.

Overheard by: Argopelter

Horny dude (after being rejected by a girl at the bar): I asked her if she wanted a drink and she gave me the look that I give to homeless people on the subway.

–79th & Broadway

Guy to girl sitting at a sidewalk cafe: I know, what is with her? She dresses like a homeless person. And not Mary-Kate Olsen homeless but I-think-I-saw-her-passed-out-in-an-alleyway-with-a-heroin-needle-sticking-out-of-her-arm- homeless.

–10th St & 2nd Ave

Girl, to guy who has just spat on floor: Don't do that! Homeless people sleep there!

–6 Train Station

Guy #1: Yeah, she looked like such a mess. Her ass was hanging out and everything. Man, if that was my daughter I would take her aside and say, “Listen. Cover yourself up. That's only for daddy.”
Guy #2: Hahaha, for sure. (pause) Wait. Say that again.

–54th St

Student #1: You can't be racist against midgets.
Student #2: What about a race of midgets? You know there were islands where scientists found four foot elephants.
Student #1: All elephants are four feet.

–NYU

Overheard by: Ajay

Teen girl: Oh, I love your nose! What nationality are you?
Middle aged man: Pardon?
Teen girl: I mean, where were you born?
Middle aged man: USA.
Teen girl: What?
Middle aged man: The United States.
Teen girl: (looks confused)
Middle aged man: …of America?

–L Train

Little kid: We're going to the city to get mommy titties!

–LIRR Train

Punk chick: This thing needs bazooms. I'm a punker chick with itty bitties.

–Midtown Office

Girl to female friend: Hey, did you know today is the three-year anniversary of my boobs?

–Union Square

Crazy lady trying to exchange a shirt: I can't go to work with my tits hanging out!

–Abercrombie & Fitch

Overheard by: me neither.

Chick on cell: In his defense, I forget about breasts, too.

–Columbia University

Overheard by: Wild Dog Boy

Asian girl #1 to Asian girl #2: Hey!
Asian girl #2 (surprised): Hi.
Asian girl #1: Haha, I recognized you by your boobs.
(Asian girl #2 laughs, her boyfriend shifts uncomfortably)

–Columbia University

Nanny: Do you still like that boy from your class?
Six-year-old girl: No! He stinks.
Nanny: Aww, what happened? He was so cute, I thought.
Six-year-old girl: I know. But he ejected me.
Nanny: Rejected you?
Six-year-old girl: Ejected me!

–Smith & 9th Station

Girl #1: What do you think?
Girl #2: Oh! He's kind of cute…except he looks kind of like a serial killer.

–Le Royale, West Village

Overheard by: Pierre Pierre

Headline by: Elise

Runners-Up:
· “Bloodstains Will Do That” – benji
· “Exactly What the Dexter Ads Were Aiming For” – Peter
· “Gossip Between Jurors at the Ted Bundy Trial” – ted bundy
· “OMG! If He Asks Me Out, I’ll Just Die!” – juls
· “The Hockey Mask Is a Nice Touch, Though.” – Sandy Paws
· “To Be Fair, She Said That About Almost Every Guy Tammy Set Her Up With Who Happened to Have a Swatstika Tattoo on His Forehead” – Rebecca Loeser
· “What With the Clown Make-up and All” – BabakganoosH
· “Why Girls Like Cats” – lucyconnuk
· “You Know, Kind Of a Lady Killer Type, Ya Know?” – c

Click here to see the new Headline Contest

Employee: I was eatin' with my fried Okra and I vomited all over your fetus…and that's why you're so ugly.

–The Strand Bookstore

Overheard by: Dazzle

Girl on cell: Oh, please! That bitch is ugly and her cooch probably smells too, he can have her! Because I don't need him or his greasy ass head or pencil dick. (pause) What? Oh, fuck you also! (hangs up and storms off)

–Columbus Circle

Overheard by: Rich

Serious gay black man on phone: Oh, please honey…there are just so many ugly white women in Europe…it's got to be something in the water!

–45th & 8th Ave

Overheard by: Culturally Challenged

20-something guy on cell: She ain't the prettiest bitch, but she got these crazy little hands.

–Throop & Macon, Bedford-Stuyvesant

Overheard by: elephantgiraffe

Hipster girl: I have ugly friends. I just don't hang out with them on weekends.

–McCarren Park Pool

Overheard by: I don't hang out with ugly people

Attractive tween to friends: And then Lindsay's aunt came into the bathroom to comfort us and said, "pretty people always get blamed for things ugly people do."

–W 65th St. & Columbus Ave

Husband to wife: Maybe we should go tanning today.
Wife: Why? Are we going somewhere?
Husband: No, it's just for you. You look fishy.

–W 4th & Thompson