Questions

Dude: Hey, good to see you, what’s new?
Goth tranny: Oh, not much. In a new band, we’re looking for a bassist, we have a show on Saturday, my apartment sucks, Joe quit, been trying to lose weight, I need a haircut, it’s my birthday next week, and I’ve been playing World of Warcraft. What about you?

–Halloween Adventure, 11th & 4th Ave

Overheard by: Kate Melvin

Woman walking out the door to man: You smoke Newport?
Man: Sure, but what I need is a blunt, yo! (pauses, looks at woman closely) Damn, you ain't Administration for Children's Services, are you?

–Queens Family Court

Lady looking at another woman's Roman sandals: I don't like those Jesus-lookin' sandals!

–The Village

Girl: Do flats make your butt look big?

–9th St & 3rd Ave

Overheard by: Matt Morgan

Guy with faux-hawk: You know in Pee-wee's Big Adventure, after he loses his bike and everyone around him is riding bicycles? I feel that way with high-tops right now.

–14th & 1st

Overheard by: Heather

(trendy, skinny, Upper West Side woman on sidewalk is staring down at her feet and looking concerned)
Preppy 30-something boyfriend: I think your toes look better in those sandals.

–86th & Broadway

Overheard by: Sushene

Girl: My uncle is gay, like, flying-out-of-his-loafers gay.

–W 67th & Broadway

Overheard by: magical-newyork.blogspot.com

Female cop to two male cops: So he's standing there, really well dressed, nice shoes, and all of a sudden he pulls out this big, big (voice drops) boner, and says "Give me the shoes!"

–Continental Ave Station, Forest Hills

Guy to girlfriend and friend: Goddammit, neither one of you is a gay man trapped in a woman's body.

–8th & 9th

Overheard by: cracking up

Girl on cell: Are all she-males gay? Cause if they're into women, sign me up.

–Astor Place

Teen on cell: Dudes have, like, purses here…

–110th & Broadway

Overheard by: Al-master

Guy to friend: She's not a tranny, but she's, y'know: tran-y.

–Grand St & Bedford Ave

Overheard by: KateM

Man on cell: You and I are both complex women. It's more complicated than that.

–21st St & 8th Ave

Overheard by: Ben

Young woman on cell: He said he just wasn’t attracted to me. What do you think he meant by that?

–60th & Madison

Overheard by: The New York Crank

Bleach-blonde: I would totally vote for McCain if Miley Cyrus were his running mate.

–Columbia University

Overheard by: Democrat

Woman: Oh, I am definitely a single-issue voter. And right now, that issue is: Which one of the candidates can get me to a bathroom soonest?

–7th Avenue, Park Slope

Overheard by: Chuckell

Drunk hobo to a group of pigeons: And they’re all Democrats. Can’t trust them Democrats.

–Washington Square Park

Young African American woman speaking animatedly on cell: … Vice president? Why should I run for Vice President, I’m doing better than you, bitch! "Dream ticket!" That’s why I hate white liberals. They don’t know when they’re fucked up. Republicans don’t give a shit about you, but they know it.

–124th St, Harlem

Drunk wheelbo, shouting across the entire ferry terminal: Hillary, Hillary, she’s our man! If she can’t do it, no one can!

–Whitehall Ferry Terminal

Lady on cell: When you done turn Governor, you can’t play dat shit…

–Associated Supermarket, Myrtle Ave, Brooklyn

Overheard by: PdQ

30-something guy to group: So yeah, I mean my ex-wife found out I bought a new car, a Benz, and that my new girlfriend was driving around in it. So she got all pissy and told me to buy her a car. So I bought her the shittiest Toyota I could find at the used car lot. No joke, this thing is a death trap. I hope she burns alive in it.
Friend: Um, don’t you have kids?
30-something guy: Yeah, so?
Friend: Doesn’t your ex-wife drive the kids?
30-something guy: Oh fuck me, now I have to tell her that I tried to kill her.

–Metro North Train

Overheard by: Just Trying to Sleep…

Mom: We can go to Coney Island this summer. It's not closed, just some of the rides.
Kid: Mom, what's a trophy wife?

–1 Train

Black guy #1: How many credits are you taking this semester?
Black guy #2: 12.
Black guy #1: Why so few credits?
Black guy #2: What do you mean, why so few credits?
Black guy #1: Yeah, why so few credits?
Black guy #2: Tuition, nigga!

–B52 bus

Overheard by: Andrea Quijano

Woman to another: Eat the penis, Danielle, eat the penis.

–New Jersey Transit train out of Penn Station

Overheard by: Tootles McGee

Black guy: Yo! Where my penis at?

–Bergenline Bus

Overheard by: Don’t know how he lost it to begin with

Guy with big dog to girlfriend: Is my cock straight?

–12th & 7th Ave

Overheard by: Amanda

Five-year-old son to father helping him ride a bicycle, seeing wooden posts out of the water: Daddy, is that a huge penis?

–South Seaport

Female suit: Their penises don’t care!

–Times Square

Hobo: I’m the unluckiest son of a bitch I know! If it were raining vaginas, I’d get hit in the head with a penis.

–5th Ave

Girl on cell: That’s good… Did you like the peen? The peen? Did you like the penis, mother? The penis? Oh good, I though you would.

–9th & Prospect Park

Overheard by: Other Side of the Fence