Union Square and East Village

Girl: I think there’s a pretty good seafood restaurant around here. What kind of fish do you like?
Boyfriend: I really like goldfish.

–E14th & 3rd

Overheard by: one order of koi, please

Hobo with two jars in front of him: Food or drugs! Choose whether you’d like to sponsor my evening shot or dinner!

–Central Park

Homeless man: Hey, bindi-a, lookin’ good today! (Indian girl ignores his comment, begins to walk away). Fine! When you get mugged, I’m not helping you!

–Washington Square Park

Enterprising lady hobo: You could use your credit card to get cash, and give me the cash.

–Outside Dunkin’ Donuts, Brooklyn

Overheard by: Rich Mintz

Panhandling hobo: Spare some change for a large bottle of water and a nice Chef salad? Spare some change for bottled water and salad?

–Broadway & 10th St

Hobo: Hey lemme borrow those red Converse! I’ve got a hot date with Monica Lewinsky tonight!

–14th & 6th

Hobo to another: "You’re gonna turn me into a waffle?" That’s what she told me, you said! A waffle? Oh no, I don’t think so!

–23rd b/w 6th & 7th

Overheard by: sara

Crazy hobo: Watch out for traffic and knuckleheads! Beware! (points at random pedestrian) Him! He’s a knucklehead! Don’t trust him!

–5th Ave & 49th St

Hipster chick: It costs like $280 to go blonde, which seems expensive but it’s totally worth it because then you’re blonde.

–Hop Scotch

Overheard by: bildita

Hipster: My brother entitled all of his college essays "Heeeey Essaaaaay!"

–Smith Street & President

Overheard by: Michelle C.

(drunk or ill hipster guy lying on stairs moans pitifully and vomits)
Hipster’s friend, looking away and pretending not to know him: Ha! Fag!

–7th Ave

Young hipster: Let’s face it, at some point I’m gonna be homeless.

–Union Square

Overheard by: Conti

Hipster girl: Pickles are so in right now.

–Renegade Arts Festival, Williamsburg

White queer to friend: So I was sitting there at the restaurant with my parents and looked to my left, and who was there? LL Cool J! Ooooh, girl, he is fine. I was all: "Hey, LL, you can park your big Underground Railroad right in my behind!"

–UES

Hipster: You can’t really enjoy Evel Knievel in the traditional sense.

–St. Mark’s Place

Nine-year old boy to another: Ooh, Indiana Jones! Look, Shia LaBeouf! I used to go out with him.

–St. Mark’s Place

Overheard by: learned something new about Shia LeBeouf

Proud teen: I had my picture taken with Dennis Rodman’s sister.

–Houston & West Broadway

Worried hipster: And I think Judge Judy would just say that I don’t have a leg to stand on.

–W 19th St

Bus driver: I know what it’s like to miss a flight. You have to ride a Greyhound bus and sit next to a fat guy who eats Cheez-Its and talks about Scott Baio way too much.

–NYAS Shuttle, JFK

Overheard by: innocent bus rider

Young male professional: So your dad’s cool with you not eating?
Young female professional: Yeah, he’s totally fine with it. He’s gonna start next week too.

–Union Square

Girl, about spiderman 3: It was a great movie if you wanted to see how to be the world’s worst boyfriend. All he cared about was himself. I mean, how could he have been so stupid? He…
Guy: You know, it’s not always the guy’s fault.
Girl: But it was! Were we watching the same movie?
Guy: I can’t believe we’re arguing about whose fault it was that Peter and Mary Jane broke up.
Girl: It was his fault.

–Union Square

Bearded guy to female friend: I went to Williamsburg and was like: "Who *are* all these people that look just like me?

–Café Pick Me Up, 9th & Ave A

Overheard by: Doibles

Young hipster: I only date girls from the Lower East Side or Williamsburg.

–9th St & Ave A

Overheard by: bildita

NYU girl to friend: Berlin is like, the new, like… Williamsburg.

–4th Ave & 12th St

Overheard by: john.ainley

Young girl: I’m Middle Eastern, and I swear to god if I see another honky wearing a keffiyeh I’m going to commit fucking Jihad on Williamsburg.

–Park Slope, Brooklyn

Visitor, looking around in bewilderment: Why is everyone trying to look like they’re poor?

–Bagel Shop, Williamsburg

Overheard by: NCT

Amazed thugette: You know you ain’t in the hood, ’cause it says "Wine & Spirits!"

–12th St & 5th Ave

Overheard by: Toto

Box office employee: I bought this really awesome bottle of wine and I was like: "Oh, I’m going to make really amazing pasta with vegetables and bullets in it and glass and blood and it’ll be fantastic." But then I didn’t.

–Pearl Theatre

Overheard by: Mariah

Middle aged white guy: Yeah, you can get cheap wine in Harlem, but who wants to get a massage there?

–Thai Restaurant

Belligerent toddler to mom making purchase: That’s not enough wine, mom! That’s not enough wiiiine!

–International Wine & Spirits, 113th & Broadway

Overheard by: McF

Hipster to his date: It’s like in the old DC Comics. Superman, you know, his weakness was Kryptonite, but there wasn’t just green Kryptonite. In the old DC Comics there was green, red, blue Kryptonite, all colors of the rainbow. Green Kryptonite killed him, but with the others, like, blue Kryptonite transferred his powers to someone else or something like that. Red turned him evil. All these different colors of Kryptonite had different properties. And that’s how wine is with me. Every glass of wine, I don’t know what I’m going to get… That analogy was not so great.

–Hope & Anchor Diner, Red Hook

Overheard by: AeC

Old man: Hah! I fell asleep at her funeral!

–3rd Ave, b/w 10th & 11th

Overheard by: j

Man to woman: Hey you! You were in my dream last night. You, myself and a bunch of people in the office were having an orgy on a mattress right in front of our office. At first it was great, but then it became awkward because people kept walking into the office and we got in their way.

–34th St & 6th Ave

Man with French accent on cell: Do we have room for her, or will she have to sleep in the dungeon?

–32nd & Broadway

Overheard by: LC

(guy is woken up by a friend after falling asleep on the train)
Guy: You dude, why you wake me up! I was having the best dream. There was shorties everywhere. There was shorties in trees and shit!

–2 Train

Conductor: For all of you running late, we are being delayed by another train with the emergency break on. Or you could tell ’em you just slept in today.

–D Train

Overheard by: blistexaddict

(goth chick runs down the street shrieking, followed by her hipster-chick friend with tiger face paint)
Young black girl #1: What’s happening?
Young black girl #2: Yeah, what’s with all the crazy white people?

–St Marks & 3rd Ave

Overheard by: Tigertail

Headline by: chrissmari

Runners-Up:
· “How Young Oprah Got the Idea for Her Show” – Doug
· “Let’s Go Back to Harlem Where It’s Safe” – Caitlin
· “Obama Better Fix That Shit His First Day” – Steve J
· “The Little-Known Eighth Sign Of the Apocalypse” – samson
· “Wait Until You Meet Dennis Rodman” – Aussie_Girl

Click here to see the new Headline Contest