Physical appearance

Guy #1: Big girls need love too!
Guy #2: Not from me, my bed is too small to fit a baby whale.

–46th St & 6th

Overheard by: TL

Perplexed girl #1: What is with that guy from Tokyo hotel? Is it a man or woman?
Perplexed girl #2: It's like a shim. I think it's like androgynous… Sort of like Pat!
Perplexed girl #1: Oh my god! That movie was the best! We should totally rent that and laugh hysterically at it. (starts singing) “It's time for androgyny, here come Pat!”

–2nd Ave

Obese girl, sweetly, to even bigger boyfriend: Honey, you're taking up two seats.
Boyfriend, very earnestly: Oh! Sorry, baby!
(he condenses his mass from three seats to two)

–7 Train

Female tourist: Hey, we're in New York City! We can let our hair down and have fun!
Male tourist: Too bad I'm bald.
Female tourist: Well, you're screwed.

–Starbucks

Person #1, in line for fitting rooms at H&M: How many people actually buy these clothes?
Person #2: A lot.
Person #1: But we live in Westbury, we'll never get to wear these.

–34th St & 7th Ave

Friend #1: I hope I never have an ugly baby.
Friend #2: Well, then don't get pregnant.

–B38 Bus

Overheard by: Paula Lanier

Size 10 policewoman: Ya know, I gotta gain some weight.
Size 14-plus policewoman: Ya can have some o' me, anytime.

–Staten Island Ferry

Overheard by: Could'a Been A Contender

Diner: How adorable! Confirmation?
Mother, with two adorable little girls in white dresses: Communion. No, wait. Baptism.
Diner: Whatever. I'm Jewish.

–Pizzeria Uno, 81st St & Columbus

Hot girl: Hmmm, that's a synecdochical headline.
Hot boyfriend: What does “synecdochical” mean?
Hot girl: Well, synecdoche is a figure of speech where a part of something is used to stand for the whole of it, or where the whole of something is used to stand for a part of it. So, in that newspaper that guy is reading, when they say, “Detroit uses bailout money,” they really are talking about the automobile industry, not all of Detroit. They're using all of Detroit to refer to a major part of Detroit's economy. Synecdoche. They use this in newspapers all the time, come to think of it.
Hot boyfriend, smiling but clearly no longer following her: Girl, look at that vocabulary! You're so smart.
Hot girl, flatly: Yes, yes, I'm very smart. Now shut up about that and tell me how pretty I am.

–6 Train

Overheard by: someone with different priorities

Girl to boyfriend: Two years ago I saw your penis under a bright blue light. And it was small.

–Penn Station

Black guy to black friend: Her father does not want his daughter marrying someone from another race. What, is he scared that the kid will come out black and have a big nose? I'll tell you one thing–he'll have a big dick.

–Bowery & 1st St

Overheard by: Zach B

Man to girl beside him: Mine isn't that big. But it's big enough for what I need it for.

–6th Ave & 9th St

Girl to friend: He had a big penis. It scared me.

–Hunter College

Overheard by: s0uthard

Young teenage boy to another: You're telling me you have an 8.5 inch dick and you don't touch it?

–M21 Bus

Overheard by: zaarah