Physical appearance

Guy: Hey, you look pretty…
Girl: Fuck off!
Guy: Don't interrupt…pretty ugly.

–C Train

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

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

Older man to African American girl): Where are you from? Ghana?
Girl (astonished): Columbus, Ohio!

–Terminal 2, JFK

Overheard by: Generous Supply

Sporty teen girl: So, I'm pretty sure Amy* is a lesbian. She never straightens her hair, and she always wears those coconut earrings…
Blonde friend: You wear coconut earrings.
Sporty teen girl: Yeah, but not every day!

–Central Park

Salesperson to customer with small dog: You know that we now have pet products?
Customer: Yes, he's using them already.
Salesperson: Oh, he looks great!

–Kiehls, 3rd Ave & 13th St

Overheard by: David Feldman

Man on subway, about to exit: Obama, Islam, Canada. Obama, in Islam, and Canada. (exits train)

–Downtown D Train

Overheard by: katiekatydid

Thug to tourists: How do you say "thank you" in Canadian?

–34th & 7th Ave

Overheard by: Fluent in Canadian

Student: I'm so sick and tired of your Canadian condescension.

–Eugene Lang College

Crazy Brooklynite at a payphone: The Queen owns everything! She owns Europe, she owns Africa, and she owns Canada! The one thing she doesn't own is the US. So could somebody give me a US quarter for a Canadian quarter?

–Broadway & 8th St

Ditzy blonde to another: Do we look Canadian?

–Chelsea

Overheard by: Holls

Big guy to girlfriend after stepping on her feet in the crowd: I'm sorry. It's not my fault I have these huge boats for feet.
Random lady: They could be canoes…

–Staten Island Ferry Terminal

Asian teen #1: I know this kid whose skin is orange. It's 'cause he grew up in Chernobyl.
Asian teen #2: What's Chernobyl?

–Stuyvesant High School

Overheard by: knows what Chernobyl is, at least