Store

Mom: You should find a nice girl to settle down with! Why don't you ask that girl you work with to dinner sometime?
Smartass teen: Because she's in her 70s.

–Serendipity's

Male customer to UPS guy: Do you have a boxcutter I can use?
UPS guy: Uhhh… no. Just use a key or something.
Female suit waiting in line: I've got a boxcutter. (pulls it out of her purse)
UPS guy: What the fuck?

–UPS

Person #1: Just take your pants off and try… please?
Person #2: No, I don't want to.
Person #1: Then why are you holding yourself?

–FAO Schwartz, 5th Ave

Mother: Do you need to buy some condoms?
Daughter: What? No, I am not talking about condoms with my mom. This will not happen. (mother drifts over to the condom shelf)
Daughter: No, no, no, no! What are you doing! Stop it! Stop it now! Oh god, you're actually considering the brands! Why are you… this is murder! You're killing me. You are actually killing me! I am going to die, and it will be all your fault!

–Walgreens

Overheard by: Moms, man.

Small child, pointing to douches: What are those, mommy?
Mischievous teen, intervening: Candy.

–Downtown CVS

Spoiled hipster girl: Yeah, like that time your mom borrowed my top to go clubbing.
Spoiled hipster boy: Well, I hope she got action in it!
Spoiled hipster girl: She did, I think she hooked up with some married man. That's why I have the money for the new top I'm getting!

–Urban Outfitters, West Village

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

Professor, seriously: Were you involved in the jelly bean incident?

–Physics Hallway, Trinity School

Overheard by: Siena

CSR: Stale peeps are excellent! Now, that is one finely-aged peep.

–Hudson & Houston

Overheard by: Harriet Vane

Man to friends sitting on bench: You either look at the girl or you look at the ice cream!

–Outside Sundaes & Cones, 10th & 3rd

Overheard by: The Girl Anonymous

Cheerful gift shop clerk on phone: So I got my peanut buttercups and then Anne* saw me on the street and came up to me, and punched me in the face and was all "Give me a peanut buttercup!" and I said "but there are only two in the package and I was saving one for Robert*!" Then she punched me in the face again!

–The Cloisters

Overheard by: Rose Fox

Greek waitress: Ice cream without whipped cream is like… girl without boyfriend!

–Diner, Bay Ridge

Overheard by: Jon A.

Black man passing out leaflets: And this woman here, you know she'd love to have a big black cock in her. Don't deny it, baby, you would.

–Outside Penn Station

Overheard by: unimpressed and skeptical

Girl to friend, unknowingly a few feet away from black guy: Thank god there's no black people on this street.

–Steinway St

Black TA, walking in five minutes before class: Oh my god, am I early? Oh, no! I'm going against my people's stereotype!

–Classroom, NYU

Overheard by: kpan

Asian guy to another, loudly: The black girl doesn't sound black. How do they do that?

–Uptown W Train

Queer to another: So I want to get dreadlocks, like black people.

–W 14th & 6th

Black lady to staring white kid: That's right little boy, this is what a black person looks like.

–Outside Toys R' Us, Times Square

Random lady #1: Yeah, they had a cream for day and another for night.
Random lady #2: Oh, really?
Random lady #1: Yeah, one for am and one for fm.

–Macy's Kings Plaza

Overheard by: Dee