Clothing

Guy: Yeah, these Speedos won’t work for me. My dick’s too big for them. They never fit right.
Shopgirl: I’ve never seen a customer with that problem. Let’s see what else fits your.. you.

–Paragon Sports, 18th & Broadway

Headline by: jgordon

Runners-Up:
· “A cock and bull story” – Guy

· “Finally, it matters.” – Ben Allaire

· “Try to contain yourself” – Jenny

· “We’ll just ignore the fact that your ass is too big for them, too” – Silvyr


· “Talk about a suspicious package…” – girlhattan

· “Clerks III: Bigger, Longer, Uncut” – JB

· “Everybody Wants to Fit In” – Dave Barnette

· “Pop Goes The Weasel” – Paul

· “He has the same problem with hats” – Kendal

· “If she keeps talking like that, they’ll fit even worse.” – bill

· “Quite a Pickle” – Dave Barnette

· “Speedon’t” – Sean McGurr

· “Too big for his britches” – suzie g

· “I am one size fits all” – twosko

Click here to see the new Headline Contest

Hot queer in suit: I swear if one more thing goes wrong, I’m just going to pull my skirt over my head and scream!

–Broadway & 51st

Guy: It’s almost enough to make me try women.

–8th between 39th & 40th

Chick #1 It’s not like I told him I wasn’t wearing underwear. He asked me. I was so offended!
Chick #2: But you don’t wear underwear, and you were wearing a see-through top.
Chick #1: OK, that’s totally not the point.

–1 train uptown platform, 28th St

Girl: So did you ask your mom if you can go to the party or not?
Guy: Oh yeah! She said yes. But she made me promise to not come home this time with no pants on.
Girl: Seems fair.

–Rite Aid, Lex Ave

Overheard by: Jack

Girl #1: I told you I finally got that bag right? It was marked down to $200 and…
Guy: My god! Can you stop talking to me, your breath stinks!

Silence until they exit at 96th St.

Girl #2 to friend: Dang, guys are mad grimey these days. He coulda been a gentleman and offered the sista a stick of gum or something.

–1 train

Overheard by: Shea

Thug #1: Yo nigga, what are they wearing in the hood these days?
Thug #2: Nigga, white on white is out!

–Outside Kenneth Cole, 5th & 17th

Tween to her mom: Oh look, it’s those shoes you can eat! Wait, can you eat them? Oh, no, these aren’t the edible ones.

–Payless, Upper West Side

Overheard by: embarrassed to have been in payless

Girl #1: So he was at my house and we were like, fooling around on my bed, and I was lying on top of him, but then I made him get up.
Girl #2: Why?
Girl #1: Because if he got turned on, got hard, came, his zipper fell down a little and some come got on my pants and while I was taking off my pants it brushed my underwear and then went inside me, I could totally get pregnant.
Girl #2: Oh, right.

–84th & 2nd

Overheard by: Samantha Thomas

Hipster girl: She was all, “Yeah, Betsy is my best friend,” and I was like, “Best friend? That is so fucking bourgeois.”

–L train

Girl: I know you made it. Look at you. You got a BlackBerry. Yeah, you made it. You got that good-smelling leather.

–Elevator, 12th & 5th

Overheard by: Thirsty Violet

Professor lady: Yes, we’ll be going into debt a lot as the semester goes on.

–Parsons School of Design

Overheard by: Ray

Teen boy: Anyone on this train wanna buy some candy? It’s not for a basketball team or something, it’s for me so I can buy more candy.

–2 train

Overheard by: Sarah

Intercom: Please take a headset before you get on the plane, because they’re free now. They’re actually free once you get on the plane, but I charge $50 labor for bringing them to you once you’re on. So it’s in your best interests to take one now. Can you tell I’m a happy person?

–LaGuardia

Chick: I’m not even gonna try applying for a Gap card; they’ll never give it to me. I don’t know what it is about Gap; they always know if you have bad credit.

–The Gap, 34th & Broadway

Overheard by: Dianora

Tween boy: What do you mean, I can’t get anything? I’m the one with a job.

–Key Food, Park Slope

Overheard by: Shack

A little tries to stuff his baseball cap in his pants.

Mother: That cap belongs on your head!
Little boy: It is on my head.

–Macy’s, West 34th Street