Teens

Old man: Let me ask you something. When you see a person in a wheelchair or on crutches, do you feel bad for them?
Teenage boy: Um… I guess, yeah.
Old man: You shouldn't, because they don't feel sorry for you.
Teenage boy: Oh. Thank you.

–Brooklyn Heights

Teen daughter: Amy Winehouse just won all the Grammys.
Father: That’s not right. They shouldn’t be doing shit like giving people in jail awards.

–26th & 9th

Trendy Dominican teen girl #1: Like, I just don't understand people who have this like, fetish about the beach. Like they looove the beach so much. I like, don't even like to go there. It's like weird, and you…
Trendy Dominican teen girl #2, finishing her sentence: …get lots of sand in your twat, yo!

–1 Train

Crazy stranger: Hey kid, you're a total cunt!
16-year-old: Gee…thanks, mister.
Crazy stranger: No problem. You like chicken?

–6 Train

Teen girl: Don't you like how my bracelet matches my shirt?
Boyfriend: Are you serious? They don't match.
Teen girl: Yes they do! What's wrong with you?
Boyfriend: I'm color blind.

–L Train

Nerd: They should have an alphabet bar… You know, where they sell you alphabets.
Girl: Wow, are you the new freak on the gymnastics team?

–Bronx Science Gymnastics Team

Overheard by: LSb

Female shopper to Bloomingdale's cologne sprayer: Don't you dare spray your $30 over my $150.

–Perfume Aisle, Bloomingdale's

Old lady on cell: I mean, it's just five million…

–Madison & 77th St

Very rich mom to new nanny, about baby in stroller: Okay, well, she loves sushi, and…

–Upper East Side

Rich teen: I asked my mom to go to Louis Vuitton with me this weekend and she was like, "we're in a recession, let's go to Dolce."

–42nd St

Overheard by: I want a m6

Label-whore eating grapes and cheese, to friend: Oh my god, I feel so rich when I eat this stuff… Oh, wait, I am.

–Paul's Cafe

Teen girl #1: Listen, if you put a dollar in a Coke machine, the thing that comes out is your Coke, right?
Teen girl #2: Yeah, but–
Teen girl #1: –I’m just saying, the father should get the baby.

–9th St & 1st Ave

Overheard by: Nicole

Grad student: It’s like Hogwarts. Witches go to Hogwarts. They don’t go to Harvard Witch Management.

–Think Coffee, Mercer & W 4th

Overheard by: this analogy makes no sense

German dude to other German dude, in rapid German: Voldemort! And Dumbledore!

–96th & Broadway

Overheard by: LeLeLe

Teen girl: He said that Dumbledore takes it up the ass. Seriously.

–1 train

Overheard by: Silverhawk

High school thug girl: Yo dead ass, Harry Potter is hot.

–Houston & Green

Overheard by: chedr

Perverted tween: I wonder how many old women are into Dumbledore. They must be like "oooooohh! Dumbledooooooore!"

–D train

Overheard by: tanechka

Drunk 20-something woman on cell: I’ve fallen off the Voldemort wagon!

–Port Authority

Overheard by: McFreaky

Teen girl #1: What if chocolate came out of dicks?
Teen girl #2: Well, then I’d pay him five dollars!

–Union Square

Headline by: MarioRPG

Runners-Up:
· “A Fine Example Of a Win-win Situation” – mike
· “I’m a Dick and Chocolate Comes Out Of Me About Twice a Day.” – Redneck Jedi
· “R. Kelly Trains ‘Em Young” – haz
· “We Could Stop Renting Those Party Fountains” – Golf Widow
· “Willy Wonka’s Splendifferous Splooge” – MiaMiaPantsonFia

Click here to see the new Headline Contest