Homeless

Hobo to couple: Right, right, so you take a donut, put it where it don't belong. Like in a tree. Now you got a tv. Take a cream cookie, wipe it on your mustache. Now you got a tv. I would put a chocolate cookie in the middle of a donut.
Woman: Oh my, where did you learn all this?

–Staten Island Ferry

Passer-by to hobo: Nice chair!
Hobo: Why, thank you, I'm a professional bum.

–5th Ave & 22nd St

Mystical store clerk to very serious customer: Yeah, I went through like half the winter like without the appropriate headbands!

–Bookstore

Overheard by: teen

Older woman to younger woman: At least you're not wearing windpants anymore. That's an improvement right there.

–Bedford Ave & N 5th St

Middle-aged businessman to two others: In my life I've seen, at most, three people who look good in spandex.

–40th St b/w 5th & Madison Ave

Teen on cell: I think we're going to need something more supportive than a fanny pack.

–113th St & Broadway

Overheard by: Jeremy

Fabulous hobo: Why does a homeless man wear couture? Because he wants to show off!

–Union Square

Sanitation worker to hobo with cart full of bags: You going to throw them away?
Hobo: Naw, I'm gonna go and do my hustle.

–33rd & 7th

Overheard by: EthanK

Gay man: You know, I have finally come to accept my sexuality.
Woman: Oh, that's good!
Gay man: I'm not even afraid to tell the world: Hey everyone! I like men!
Overhearing hobo, with a hopeful smile: Hey! Me too!

–Times Square

Overheard by: hobos are around at the strangest times

20-something female on cell: But never have I ever had sex with a dirty talker before, so it was something else, to say the least. I signed up to get laid, not play Penthouse Mad Libs.

–23rd St & 5th Ave

Customer, after placing order: …with hardboiled eggs.
Gay waiter: Hardboiled eggs smell like dirty assholes, an I've seen a few dirty assholes.

–Denny's

Overheard by: student-19

Preppy guy on cell: No, dude! I don't know, like…like really dirty girls.

–86th & Lexington

Overheard by: Anne

12-year-old boy to mother: The bum, you know! The dirty man that plays with me.

–Forest Parkway

Overheard by: Jason A

Guy dancing on new lawn: This isn't even good grass! It's dirty, yo!

–Pratt Institute, Brooklyn

(lady with 12-15 hula hoops walks onto subway and sits across a sleepy hobo)
Hobo, surprised: Oh! Why you have all those hula hoops?
Hula hoop lady: Oh, well, I'm a professional hula hooper…seriously!
Hobo: Nah, nah, I see it.
Hula hoop lady: I teach a class with hula hoops.
Hobo: Yeah… (very matter-of-fact) I see the physicality of it. (Hobo gets up and does a gyrating hula hooping motion for five seconds)
Hula hoop lady: Yeah, people really get into it.

–L Train

Overheard by: Rock the Red Sock

PETA representative: Excuse me, ma'am, do you have a minute for animal rights?
NYU JAP: I'm wearing leather boots. Do I look like I give a shit about animal rights?
Panhandler: (applauds)
NYU JAP: (gives panhandler a quarter)

–8th & University

Overheard by: byron

Hobo: Do you have a small sample?
Barista #1: We're not giving out any samples.
Hobo: Do you have a cup?
(barista hands him a cup, hobo starts to walk to back of store)
Barista #2: Sir, where are you going?
Hobo: To the bathroom.
Barista #2: We don't have a bathroom.
Hobo: Can I have some water?
Barista #2: No! And do not come back here! Have a nice day!

–Starbucks, Penn Station

Overheard by: BK

Girl to friend: I helped a tourist the other day. That's not me, I'm a bitch.
Hobo, eavesdropping : Yeah, you are.
Girl: What?
Hobo: You're a bitch.

–Union Square