Hobos

Suit lugging huge rolling suitcase to hobo taking up two seats on train: Pardon me.
Hobo (sliding over, looking at huge suitcase): What do you have there, a dog or something?
Suit (with deadpan look on his face, stroking suitcase fondly): I used to. (sighs)
(hobo slowly inches away)

–L Train

Overheard by: Cai

Guy preaching on subway: I noticed I would always get hit on by beautiful women when I was with a woman, so I started hanging out with lesbians, and now we pick up women together.

–1 Train

Overheard by: Alexis

Panhandler going through train: God bless you, will anyone spare some money? God bless you, damm! You have a pretty white girlfriend.

–6 Train

Overheard by: Jackie

Woman giving out free loot: You girls are so pretty, want some condoms?

–Grand Central Station

Hobo: Why do rich men get to marry all the pretty girls, kill them, and get away with it?

–125th St

Trashed girl, coming out of bathroom: I hate when guys say, "you're pretty enough."

–Bar 9, 54th & 9th

Overheard by: Ladle

Big slobby schlub, loudly talking to buddy: So, she was about to become another disposable pretty girl.

–W 66th St

Overheard by: Susan Volchok

Rambling crazy man: All of you women look beautiful, but in the end, y'all still have to take a shit!

–L Train

Overheard by: The City Planner

Panhandler: Hey, Red, can you help me out with some change?
Red: Sorry, man, not today.
Panhandler, frustrated: C’mon man, it’s always ‘not today’ every time I see you!
Red: I ain’t lied to you yet, have I?

–Ft Greene, Brooklyn

Overheard by: Breck

Guy: 100 bucks! Can you believe it? 100 bucks and all I had to do was suck on his toes for a while!

–Soho

Overheard by: J. B. Palka

Hobo preacher: You might as well just start wiping your ass with your
college diploma, because that’s all they’re good for anyway.

–Union Square

Smoking hobo: Hey man, can I get a cigarette?
Smoking man: You're already smoking one.
Smoking hobo: Gotta plan for the future!
Smoking man: Now you wanna plan?

–12th St & 1st Ave

Overheard by: Jay

Hobo: Where are you going?
Drunk guy: Bermuda. I’m connecting to the plane.

Drunk guy: Is that your cousin?
Hobo: Yeah!
Drunk guy: He didn’t even say nothing to you. That’s fucked up!

Hobo: My name is Peter. Peter Parker. I’m Spider-Man’s father.

The hobo shows the drunk guy his bottle. The drunk guy takes out a can of beer and a bottle of whiskey

Drunk guy: So what? You trying to beat me? You started a competition and I beat you. I came prepared.

–PATH train

Overheard by: Tony Gabriel

Girl: [In the month of October] Why is there a leprechaun passed out on those steps?
Friend: Oh, wow. Is it April Fools’ Day?

–Madison Ave

Hobo: Hey buddy, can you spare a nickel?
Cabbie: Yeah, do you accept credit cards?
Hobo: Fuck you! I am here trying to live on the streets. Just take your customer wherever she’s going…Don’t you tip his sorry ass. He’s a racist Iraqian.

–23rd & 2nd

Overheard by: Cat

Yuppie giving panhandler change: Don't do drugs.
Panhandler: Where am I going to buy drugs for a quarter?

–105th St & Broadway

Overheard by: matthew

(tiny Asian girl in a striped skirt and high-heeled boots is hauling a suitcase up the stairs from the subway).
Hobo: You know who you look like?
Asian girl: Who?
Hobo: You know who you look like?
Asian girl: Who?
Hobo: Girl, you look like Paul Lynde.

–12th St & 7th Ave