Hobo: Spare some change?
Girl: Yeah…so you can go buy booze? Keep dreaming, bucko.
–Times Square
Hobo: Spare some change?
Girl: Yeah…so you can go buy booze? Keep dreaming, bucko.
–Times Square
Preppy guy: They say beggars can't be choosers, which makes sense, because we're choosers.
–Madison Square Park
Overheard by: Annie
Red Table change collector guy: Help feed the homeless of New York! All it takes is a penny and a heart, you fucking assholes.
–Times Square
Overheard by: Bemused
Girl to friend: I thought of you the other day; I saw a homeless man's penis.
–Lucky Jack's, Orchard St.
Overheard by: Argopelter
Horny dude (after being rejected by a girl at the bar): I asked her if she wanted a drink and she gave me the look that I give to homeless people on the subway.
–79th & Broadway
Guy to girl sitting at a sidewalk cafe: I know, what is with her? She dresses like a homeless person. And not Mary-Kate Olsen homeless but I-think-I-saw-her-passed-out-in-an-alleyway-with-a-heroin-needle-sticking-out-of-her-arm- homeless.
–10th St & 2nd Ave
Girl, to guy who has just spat on floor: Don't do that! Homeless people sleep there!
–6 Train Station
Hobo #1: But that's not enough to have pee in my butt…
Hobo #2 (interrupting): What would have been enough? 30, 40 dollars?
Hobo #1: Huh? Well! What the hell are you asking for? Now, exactly, you can pee in my butt for nothing…for a conversation… for a howdy do!
–YMCA
Overheard by: German Deter
Drunk hobo: Can I tell you one thing before I die? Babe Ruth was the best there ever was… But I never saw him, and neither did you! Do you know why?
Blonde girl: No…why?
Drunk hobo: Because you weren't alive…and neither was I. (takes out flute and plays Take Me Out to the Ball Game)
–E Train
Hobo to another: Ohh… Check that out! Hot white ass!
Girl in blue pants: Why are there so many drunken perverts in Central Park?
Friend (seriously): He's probably just color blind.
–Grand Central Station
Headline by: dwasifar
Runners-Up:
· “…Or, Knowing Your Ass, Just Plain Blind.” – EddieA
· “Because Let’s Be Honest, He Clearly Wasn’t Referring to That Wagon You’re Dragging.” – Wilkeson
· “Or It Could’ve Been the Ablino Donkey Behind You…” – Krikit
· “Smurfette Swore She’d Never Come Back to the City Again.” – 1310 (formerly SNA)
· “The White Pants…Always Keeping the Colored Pants Down” – California Dave
Hobo, interrupting a guy and a girl: Excuse me, could I bum a cigarette or get some spare change?
Young man: I'm low on cash and sorry, but I have a cigarette for you. (hands hobo a cigarette) Do you need a light?
Hobo: Nope. (walks away)
(young man and woman continue conversation, hobo comes back and interrupts again)
Hobo: Can I ask you a question?
Young man: Shoot!
Hobo: What does Matt Damon's dick look like in Audrey Hepburn's ass?
Young woman: Trick question.
(hobo gives them the finger, walks away)
–Central Park
Black hobo to passing tourist: Where you from?
Tourist: Ireland.
Black hobo: You Irish?
Tourist: Yeah.
Black hobo: Well, god bless the Irish. And god bless the Italians. And fuck everyone else!
–8th Ave & 22nd St
Overheard by: Doug Tischler
Old drunk hobo to friends: Let me tell you guys a story. Back when I was breaking in to fucking cars this broad comes at me and takes me to this commune. Gotta be at least 50 hippies, everyone's fucking everyone, always blazed, I'm fucking everything that moves because I'm 18 and my dick is hard all the time, and all the women are walking around all fucking…
All friends together: Naked!
–4th Ave & 13th St
Overheard by: rpk
Professor, to deaf student's interpreter: Do you deal with "fuck" and "shit" and all that?
–Pratt Institute
Mother to bickering daughters: Let me tell you something: you two bags are the only motherfuckers I got left!
–21st St & 35th Ave, Astoria
Overheard by: Daniel Boris Dzula
Young woman in burqa on cell: And Jesus Christ! What the fuck was that bitch thinking?
–Brooklyn
Overheard by: ABrooklynBaby'sNanny
Girl on cell: And he said, "I am trying to learn here!" and I said, "fuck you!"
–112 & Broadway
Overheard by: Nathan
Hobo: I was in Nantucket when I lost my bucket! Then I said, "fuck it!"
–Union Square
Overheard by: Stacy
Woman crying to friend: I don't want to do the fucking SAG Awards!
–Bryant Park
Hobo #1: If I was a robot, see…
Hobo #2: Yeah, yeah…a robot!
–91st & 5th
Overheard by: Adam
