Compliments

Charity worker: Help the homeless! [Androgynous person walks by] Even a pretty girl… boy… whatever-that-was can help!

–Times Square

Chick, wistfully: That was Vadim. He was from St. Petersburg. When we broke up he stole all my dresses.

–A train

Overheard by: Rose Fox

Large black security guard, inspecting guy’s Sephora bag: You da man!

–Hayden Planetarium

Pierced 20-ish chick: So, the last time I pegged a guy he wouldn’t stop jabbering on and on about how much he loved trannies. It just made me shove in the strap-on harder.

–Delancey & Orchard

Overheard by: Californian

Guy: I sirred a ma’am today. But, in my defense, she was a very sir-able ma’am.

–33rd & Broadway

Guy #1: He almost got married to a 15-hundred-dollar a night hooker!
Guy #2: Really? So, what broke the deal?
Guy #1: He found out she was a 15-hundred-dollar a night hooker.
Guy #2: He wasn’t paying her the whole time?
Guy #1: Naw, he was getting it for free!
Guy #2: Awesome.

–122nd & Broadway

Older drunk, tightly hugging young guy: … And don’t think I’m gonna forget. When that happened, who gave me new underwears and washed my ass?
Younger guy, trying to get away: Man, just forget about that!
Older drunk: No! I’m not gonna forget about that!

–Greenpoint, Brooklyn

Creepster #1: So, I wrote her an e-mail that said, ‘Your titties look really nice. They look really succulent.’
Creepster #2: You wrote ‘succulent’?
Creepster #1: Yeah, I said, ‘Your titties look succulent in photo number five.’
Creepster #2: That’s fucked up.
Creepster #1: I know, but…

–Union & Smith, Brooklyn

Overheard by: crowin

14-year-old girl: How long does Accutane take to work?
Dermatologist: Before you know it, you’ll be so beautiful you’ll be beating off all the guys.

–Dermatologist’s office

Little girl: You’re the most beautiful girl in the whole world! [Mom smiles.] You are.
Mom: I think you’re the most beautiful girl in the whole world.
Little girl: Only to you.
Mom, holding up girl’s art project: Actually, I think she’s the most beautiful girl in the whole world.
Little girl: No! She’s a princess bird-fish!

–F train

Overheard by: Actually, I’M the most beautiful girl in the world

Woman to Eric*: Are you a sexual adventurer?
Man: Eric is the Amerigo Vespucci of ass play.

–Against the Grain, East Village

Overheard by: Adam

45-year-old man: … And since I’m on my way to a business meeting, this drink I just bought you is tax deductible.
College girl: Well, that’s nice, I guess.
45-year-old man: Yeah, you’ve got a big butt and you’re tax deductible. That’s how I like them.

–Coffee Shop Bar, 14th St

Headline by: Snark Sloper

Runners-Up:
· “Accountant Pickup Line #65337-2366-26637-1” – Works For Me
· “Baby Got Back. — Cf, Form 1040 Schedule C Line 27” – chris
· “Monica Lewinsky: This Sounds Familiar…” – D. Kareem
· “Until She Capital Gains All That Weight” – Vasyl

Click here to see the new Headline Contest

Hipster chick, with gun charm on necklace: Can I get a Diet Coke?
Greek clerk: I like that gun. It looks like the one I keep under my mattress.

–Canal & Eldridge

Chick to another: She’s a weed-smoking, modern orthodox girl. I mean, I don’t think she goes to her rabbi’s high, but…

–Brooklyn Museum

Overheard by: cole

Professor: … So the art department on the set just smokes pot all day and paints blue boulders.

–Media Productions class, City College

Mini thug: Yo, I wouldn’t even have to be high out of my mind to enjoy this shit!

–Brooklyn Cyclone, Coney Island

Overheard by: Alie

Smoking model on cell: Um, yeah, he’s cute… But, duh — he’s addicted to opiates!

–Houston & Laffayette

Overheard by: Jake

Hobo to girls: How are you smiling in a city filled with a million crackheads?

–56th & 5th

Guy on a rant in front of Imagine mosaic: In my next life I want to be an amoeba! Make more music, smoke more pot… Eating healthily is expensive! We should all have 40 acres and a mule and start all over!

–Strawberry Fields, Central Park

Overheard by: I’ll have what he’s having