Prison

Everyone's Had at Least One Crazy Wednesday One-Liner

College girl to her boyfriend: Yeah, but you always make sexual advances on my roommates.

–Lincoln Center

Serious student: Yeah, well, I really don't want to talk about my roommate's penis anymore.

–LaGuardia & Washington Square South

Chick to friend: It's not about the toilet paper, his roommate only used baby wipes.

–Spring St & Mott St

Overheard by: Nick Caylor

NYU kid on cell: I'm still hoping to live in housing next year unless my roommates find out that I got arrested.

–Mercer & Waverly

Young suit into cell: You pissed on my toothbrush!? What the fuck? Fine, I'll get you a new pouffe… Fuck you! Pink or purple? Just get me a new toothbrush! You know what kind! Always, right? The blue ones or the yellow ones? Well, did you get your period or no? Okay… Okay… fine… fine… fine! Look, I'll be home around seven, okay? (yelling) I don't care who you're fucking, it's your turn to cook! Right, fine, talk later, okay? (hangs up, to very attractive female companion) She's really just my roommate…

–82nd & Lexington

If You're Sober Enough to Remember All That, It's Time for Stiffer Drinks

(outside bar)
Guy #1: It's your round.
Guy #2: No, it's not! Remember… I bought the first round because Paris Hilton went to jail. Then you bought a round because LeBron James had a kid. Then I bought a round when we figured out that the US Open was in Pennsylvania!
Guy #1: You're right! This round's on me!

–33rd St & 3rd Ave

Wednesday One-Liners Won't Be Buried in the Jewish Cemetery

Girl on cell (reading US Weekly): Hey, Pam Anderson and Tommy Lee were photographed together! That means there's still hope for me and that guy from the tattoo shop!

–Brookyln Diner, Times Square

Latina: What's with grandma keeping gettin' tattoos that show?

–Uptown 1 Train

Overheard by: Justin Case de Foodisbad

Chick to another: The only thing he better get tattooed on his butt is my name!

–Times Square

Overheard by: Angela

Guy to girlfriend: Does that guy over there have a picture of Kim Jong II tattooed on his shoulder? (pause) Or is that his kid? (pause) Cause that's fucked up!

–Brighton Beach

Overheard by: Not sure myself…

Girl: So I hooked up with this guy who had a prison tattoo of an eagle ripping up the communist manifesto. I was like: "God bless America," y'know?

–N train

Overheard by: amen

Mr. McCain’s Co-Workers Have Grown Weary of That Line

Hardhat to ticket agent: Yo, what time you get out?
Ticket agent: At one.
Hardhat: Me too. It’s great gettin’ out at one.
Ticket agent: Yeah, but I got class after.
Hardhat: Well, better than bein’ in a Chinese prison camp.

–Water-Taxi Booth, Queens

Overheard by: obviously not as high as he is

Great! …Same Time Tomorrow?

Fat crackhead woman: Where you been?
Well dressed businessman: Around… Where you been?
Fat crackhead woman: Lockup!

–Starbucks, Harlem

Overheard by: Ryan J

But Water Balloons Are My Art Form!

Dude #1: They don’t give you condoms?
Dude #2: Naw, they don’t.
Dude #1: You serious, man? No condoms?!
Dude #2: Yeah, I’m serious — they don’t give out condoms!
Dude #1: Really… They don’t give you condoms in prison, huh?
Dude #2: Naw, man, not unless you have conjugal visits or somethin’.

–M11 bus

Grandma, What Big Wednesday One-Liners You Have!

Girl on cell: Stop talking about my grandmother’s ba-donka-donk!

–6th & 2nd

Girl on cell: So, she walked in on me getting out of the shower again this morning… Yeah, I guess I could put a lock on the door, but I’m really starting to think that my grandma just likes seeing me naked in the morning.

–School of Visual Arts

Overheard by: dobby

Chick on cell: What should I get for Grandma? No, I’m not at a mall, I’m on the street… No, I don’t see anything she’d like, unless… Do you think Grandma wants a bong?

–St. Mark’s Pl

Overheard by: Heather

Dude to hot chick: I’d rather have sex with you than my grandma.

–1 train

Overheard by: bldlube

Guy on cell: So then he’s like, ‘Dude, are you in prison again?’ And I was like, ‘No, dude, I’m talking to you online. How could I be in prison?’ And he was like, ‘There was a computer when I was in prison. I mean, you had to suck dick to get online, but whatever.’ And I was like, ‘Dude, I’m at my grandma’s house. We’re having tea and shit.’

–E 14th St & Irving

Wednesday One-Liners Sharpen Their Shanks

Thugette on cell: Yeah, I’m planning on getting arrested this weekend. That’s my new thing now. Instead of going to the club and shit, I’m just going to get arrested.

–34th & 8th

Overheard by: Clitoris Rex

Metrosexual: Oh my god! Did you hear that Paris Hilton just escaped from prison?

–Broadway & Prince

Mom eating fried chicken: I always thought Penn Station stop was named after a penitentiary…

–A train

Overheard by: Denning

Mocking cop to dude he just arrested: You’ve got jail!

–West Village

Either She’s Packing Heat, or His Name’s “J”

15-year-old preppy #1: I think Lisa’s really cool. We should hang out with her more.
15-year-old preppy #2 Yeah, she seems like a really cool girl. I guess her boyfriend’s in jail or something… And she has his name tattooed on her clit [gestures to stomach area] or something…

–Atlantic Ave

So, How Long You Out For?

Drag queen: Hey, were you in prison?
Angry man: Yeah, I was.
Drag queen: That’s where I know you from!
Angry man: Oh, yeah, hey! How are you?
Drag queen: I’m good. It’s so good to see you!

–E train, 42nd St

© 2026 OverheardinNewYork.com
Hat Tip 🎩 to The Marketing Scientist