Gender issues

Straight Jewish boy: Oh, man, with going now to see the Assassination of Jesse James by the coward Robert Ford, plus I saw 3:10 to Yuma last week, I’m going to have seen two westerns in the past two weeks. I feel so manly.
Hipster girl: Don’t worry, we can go get you a throw pillow later.

–Outside the Angelika

Middle-aged black woman: William Shatner should run for president or governor or mayor or something… He’s got the charisma.

–Staten Island Ferry snack bar

Overheard by: Stephanie

Hobo spinning in circles: ‘Bout time we got some poontang in the White House! There’s a first time for everything!

–117th & Broadway

Overheard by: Vicksburg

Thug, watching Elliot Spitzer and Chuck Schumer drive by: Who da fuck these niggas?

–Super Bowl Parade

Overheard by: No idea

Scholar: I’m voting for Osama Barack.

–F train

Overheard by: Terrorized

Conductor: Grand Central Station. Two and Three trains across the platform. Change here for the Seven, A, C, E, and shuttle to Times Square. Vote Obama.

–1 train, Grand Central

Drunk guido during post-Super Bowl rioting: I mean, who cares who the next president is after this?

–52nd & 2nd

Overheard by: NCS

Chick: I would like to become a boy for a day just so I can pee standing up.
Guy: I am not going to lie to you, it’s awesome!

–Georgia Diner, Queens

Five-year-old girl: … And then he changed seats!
Nanny: Why are you obsessing?
Five-year-old girl: Because boys are weird.
Nanny: Boys will always be weird.

–29th & Park

Overheard by: Adam Nathan

Hobo, singing: If you want my body, and you think I’m sexy, baby won’t you tell me so?
Tourist woman: You go, girl!
Hobo: Yo! I’m a guy!

–R train

Old lady, to two-year-old: … And what a sweet little girl you are! [Lady turns to child’s father] It’s nice to see that in this day of child molesters and perverts your daughter isn’t afraid of playing with complete strangers.
Old lady’s old hubby, whispering: Honey, that’s a little boy.

–La Bagel, 15th & 1st

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

Man: So, you think I can’t understand because I don’t have a vagina?
Lesbo: Don’t sit like that!
Man: What do you mean?
Lesbo: You’re crossing your legs so condescendingly!

–Tea Lounge, Park Slope

Overheard by: Lemma

Headline by: Manbo

Runners-Up:
· “Almost Enough to Make Up for You Lack Of Vagina” – John Gray
· “I’m Just Jealous Because Mine Are Too Fat to Cross That Perfectly” – shenanigans
· “I’m Just Protecting My Tool Of Oppression.” – robs
· “Well You’re Waving Your Vagina Condescendingly” – burnt toast
· “Worst Yoga Class Ever” – benji
· “Yeah, Well Tell Your Nipples to Quit Pointing at Me” – pw

Click here to see the new Headline Contest

Hardhat #1 with pavement-smoothing machine: It won’t start.
Hardhat #2: I tell ya, if it’s got tits or wheels, it’s gonna give ya problems.

–75th & 3rd

Overheard by: Mo

Impatient, middle-aged Caribbean woman in bathroom line: There should be more women’s rooms.
Equally impatient 20-ish woman: Yeah, I know… It’s because men designed these buildings.

–JFK

Overheard by: Nina