Guys

Hip Hop girl: Why do we always judge people on how they look?
Hip Hop boy: We’re not judging them. We’re judging their looks.

–42nd & 8th

Ditzy college girl: Yeah, but I’m like a fun drunk, right?
Guy (serious): Ummm… Well, you were kind of saying that life has no meaning and that it’s not worth living.
Ditzy college girl: What?

–Union Square

Overheard by: Gaby

Guy # 1: Dude, I’m hella hungry.
Guy # 2: I’m freakin’ hella tired of your whining, a-hole!
Guy # 1: At least I ain’t hella stupid!
Guy # 2: And you’re hella ugly!
Passenger, to guys: Are you from Jersey?

–C Train

Overheard by: Hammer-head

Guy: Just know I chose my own fate: I drove by the fork in the road and went straight. Isn't it deep? I'm getting it tattooed on my shoulder.
Girl: Who are you quoting?
Guy: Jay-Z.

–34th St, Penn Station

Overheard by: No Lie

Headline by: Lauren

Runners-Up:
· “”99 Problems But a Bitch Ain’t One” Was Taken” – Cass
· “Just How Big Is Your Shoulder?” – porter
· “Maybe You Should Tattoo That Between Your Legs…” – LPS
· “Monkeys With Typewriters Couldn’t Ever End Up With Gold Like That” – Caitorade
· “The Confucious Of Our Generation” – Fresca

Click here to see the new Headline Contest

Dude #1: Oh my god! Did you hear about Jack*?
Dude #2: No, what?
Dude #1: [Excited whisper.]Dude #2: He’s a what?
Dude #1: [Enunciates whisper.]Dude #2: No — a hobo is a homeless person.

–LIRR

Mother to screaming child: Please stop crying and put your coat on. I am not hurting you or torturing you, so please stop crying.

–4th Ave, Brooklyn

Overheard by: olivejuice

Father to kid who just started crying: Hey, stop! I thought I told you to wait until we got home!

–Park Slope, Brooklyn

Overheard by: Lucian

Guy to girl, on Valentine's Day: You look fat when you cry.

–Cobble Hill

Overheard by: MJB

Hispanic man on phone to girlfriend: Ma, why you cryin?! You should be breaking up with me because I hit you!

–Staten Island Ferry

Guy to girlfriend: I'm sorry I pulled your hair while you were crying.

–Bowery & 2nd

Middle-aged woman: I really never cared for skiing, but I was so alone in my marriage, I found it was a great way to meet men.

–Burritoville, 77th & 2nd

Meathead #1, to meathead #2: Hey! Want to go to a ballroom club?

–47th & Madison

Guy, to passersby: Game of chess? Play chess? Chess?…Also got chronic.

–Washington Square Park

Overheard by: Phil

Guy #1: There’s just no place to go dancing, you know?
Guy #2: You can’t find a dance club in New York?
Guy #1: No, it’s just not right –I really like to Lindy.
Guy #2: …
Guy #1: …
Guy #2: Dude. Where the hell do you learn to Lindy?

–34th & Broadway

Straight guy: Shit! They’re closed. There’s no way I’ll be able to buy a dildo this late at night.
Guy walking by: Dude, in this city you can definitely find a dildo this late at night.

–13th St & 3rd Ave

Overheard by: Jesse D

Disgusted girl: It smells like rats!
Guy: No, it's just shit you're smelling.

–St Mark's & Ave A

Overheard by: j