Preppies

Hobo: Happy birthday! Can I have a dollar?
Preppy guy: What? Sorry, I don't have any cash.
Hobo: I accept all major credit cards.

–Columbus Circle

Overheard by: cmtWHAT

Headline by: eeny

Runners-Up:
· “…Except Diner’s Club, I Have Standards, You Know” – DotTim
· “As Unemployment Rises, Technology Transforms the Bum Sector” – PeterG
· “Hobos: They’re Everywhere You Want to Be” – Coyoty
· “Mastercard: Avaliable in More Places” – MaccasGirl

Click here to see the new Headline Contest

Preppy girl: Well, then it gets hard, duh!
Preppy guy: But… Oh… Oh!

–5th Ave

Overheard by: Angel

Hippie girl: Free hugs! We're giving out free hugs today! (to preppy guy on park bench) Hey! Would you like a free hug today?
Guy: No, thank you.
Hippie girl: Why not?
Guy: Actually, I just had a minor surgical procedure on my abdomen. I shouldn't hug anyone until it heals.
Hippie girl: Well, that sucks. A hug might make you feel better, though!
Guy: I'm pretty sure that a hug would open up the incision on my abdomen from the surgical procedure. I'm told this would increase my odds of infection. Thanks anyway, though.

–Union Square

Overheard by: Double-M

Guy: The thing about Cronenberg is that you have to appreciate him in
context to what he does…which is often unappreciable.

–Belmont Lounge, East 15th Street

Preppy girl #1: Where's that Obama book?
Preppy girl #2: The Audacity of Hope?
Preppy girl #1: Yeah, that one.
Preppy girl #2: Why do you want that? It's not like you're gonna read it.
Preppy girl #1: I know, but I feel like if I did, I'd be a lot smarter, you know?

–Strands Book Store, Union Square

Preppy tween #1: You know, I really should try to get my grades up.
Preppy tween #2: Why's that?
Preppy tween #1: Well, if I did better in school my parents probably wouldn't think I was going out and having sex and doing drugs all the time.

–1 Train

Slightly drunk kid from Alaska: I realized I had blacked out when I woke up on top of my sister.

–14th St

Overheard by: The Reverend

Young girl on cell: You passed out from him choking you? (pause) Like…does it…um…sting? Did he apologize at least? (pause) Ya know, it's not okay to get so fucked up that you don't know that he's choking you.

–Max Cafe

Overheard by: D to the ana

Loud girl on cell: Oh my god! Don't even worry about hitting on her too much, she was totally blacked out last night!

–Whole Foods Union Square

Overheard by: bildita

Preppy girl: Is "faint" a euphemism for "boner"?

–LaGuardia Airport

Overheard by: Diana

Preppy guy: Libertarianism has nothing to do with showing your breasts.

–Uncle Ming’s, Avenue B

Overheard by: Djlindee

Preppy girl: He was nice — really successful, owns his own apartment… I just wasn’t into him. He kept trying to hook up and I just wanted to be left alone. He proceeded to jerk off into his pajama pants. Oh, and by the way, it took about 40 seconds. I didn’t even have enough time to react. He then rolled over and went to sleep in it! The worst part is that he’s still calling me. Hello, buddy — you jerked off into your own pants and slept in your own cum. Yeah, we’re not gonna work.
Guy friend: That’s awesome! Who can I tell next?

–47th & Lex

Dartmouth boy: This girl I used to work with wore too much eyeliner — She was from the Midwest, she has a smile only a horse could love, skips around with lots of boyfriends, threw a birthday party for her dog — you get the picture. So she’s an ugly Midwestern girl who works at Goldman Sachs in the Muni Department, it’s not even real banking…

–Union Ave & Scholes, Williamsburg

Overheard by: Columbia Girl Who Can’t Stop Laughing