Guys

Girl: What I really want is a guy who is kind of skinny and almost homosexual.
Fat male passerby: I can be that guy!

–14th & 2nd

Headline by: h

Runners-Up:
· “But One Who Isn’t a Scientologist and Didn’t Star in the “Mission Impossible” Movies” – Hostrauser
· “Drew Carey Believes He’s a Hipster.” – Stephalee
· “I Can Be Seven Of That Guy” – Belvedere Jones
· “I’m Not Skinny, but I’m All the Way Homosexual–it Balances Out.” – KarenD
· “It Was Rosie O’Donnell” – Jess K.

Click here to see the new Headline Contest

Youngish man: What does it all mean?
Female friend: What? Life?
Youngish man: Yeah.
Female friend: Poorly maintained leather for the most part.

–11th St & 3rd Ave

Overheard by: Sukhdev

Black guy #1 to passing white girl: Where’d you get that nice big ass? Your mother give you that ass?
Black guy #2: Naw, man. White girl don’t wanna hear she got a big ass. Only black girls wanna hear that shit.

–Columbus Circle

Overheard by: DZW

Woman: And how are things with your girlfriend, hm? What is she like?
Guy: Well… she does have a big nose.
Woman: Her nose? Why are you concerned about her nose? It's her personality that matters!
Guy: But she always hits me whenever I mention it!

–5th Ave

Overheard by: the art major

20-Something dude #1: Do you still use “lol” online?
20-Something dude #2: Nah, I use “omg” instead.

–10th St & 7th Ave, Park Slope

Waiter: Hey, wassup? I’m Sean. What’s your name?
Girl: Rebecca. Nice to meet you.
Waiter: And you, man?
Guy: Kwanzaa.
Waiter: Hey, by any change you are mixed with Jewish?
Guy: Er, no, everything but.
Waiter: Well…’cause, you know, I’m Jewish.
Guy: …Okay.
Waiter: Uh, ’cause you know, Kwanzaa’s a Jewish Holiday?
Girl: It is? Wow, I didn’t know that.

–Diner 24, 8th Avenue

Overheard by: enkie

Guy, to girl: Smart girls are never pretty. That’s why you’re a dumbass.

–Union Turnpike station platform

Overheard by: Erna

Hobo: Ain’t no good here, only cheap. Cheap, cheap, and very cheap. And very beautiful.

–L train, Bedford Ave station

Chick: Where are we going?
Guy: The Junction.
Chick: Why are we going to the Junction?
Guy: Because you’re a loser. Because you question me.

–D Train

(Asian tourist walks onto subway with large panda-head shaped hat)
Random guy: Take off that silly ass hat!

–Uptown 1 Train

Guy: When I wear my other coat, I look like a yak.

–Mott St

Overheard by: robin

Thug to friend: I totally know fashion designers. I know who Hill-finger is.

–Thompson Street, SoHo

Drunk guy to orthodox Jew: Nice lid.

–Near Herald Square

Guy walking out of subway: Then she came in and told me to put the mask on.

–6 Train

Overheard by: Sarah

History teacher to class: Now, if you want a decent straw hat, do not make one.

–Millennium High School

Overheard by: Adriana

Polish guy: Dude, it smells like a midget's ass over here!
Friend: How do you know what a midget's ass smells like?
Drunk guy: He's Polish! How else would he be able to screw in a lightbulb?

–Williamsburg, Brooklyn

Overheard by: POLA