Dating

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

Gay thug #1: I wasn’t hitting on you, I was still with my ex-boyfriend then.
Gay thug #2: Then? Nigga, I wasn’t even gay eight months ago.

–Wendy’s, W. 3rd Street

Overheard by: Lizzy Vegas

Chick: I am so gonna marry your friend Chris!
Guy: You can’t. He’s gay.

–Union Square

Girl: …and he was like so interesting. We talked all night long, and I was thinking I’m so gonna marry this guy–
Guy: Oh, honey. You can’t.
Girl: Why not?
Guy: I’m dating him.

–42nd & 8th

Bald, dorky white guy on date: What kind of Italian restaurant doesn’t have Chicken Parmesan on the menu?
Homely-looking white girl on date: I know.

–Isola, 83rd & Columbus

Girl #1: I just don’t think I’m his type. He’s very intellectual.
Girl #2: What do you mean?
Girl #1: He’s all “yada yada yada” and I’m very “What’s your favorite Starburst?”

–Cosi, 31st & Park

Overheard by: Clara

Girl #1: Ha, ha, you said first was the worst.
Girl #2: No, I said, “first was the burst.”
Girl #1: What the heck does that mean?
Girl #2: It means…Starburst.

–M104 bus

Overheard by: Fatty McFingers

Brooklyn guy to buddy: Man, that chick is the hottest chick in the whole world. Well, except one — Ariel. Ohhh, Ariel. You know, the little mermaid?

–31st St & 7th Ave

Overheard by: Will

Guy: Man, if a girl is hot enough that you want get with her, and she’s single… You know she’s gotta be fucked up in the head.

–C train

Girl on cell: Oh, yeah, he was so hot. I made eye contact with him, like, two times, so I guess we’re basically dating now.

–Port Authority

Overheard by: Audrey Monaco

Trendy teen: Down Syndrome is so hot right now!

–Tompkins Square Park

Woman on cell: But how hot can a cactus get?

–Bed, Bath & Beyond

Overheard by: Ladle

Guy: You only think she’s hot because her family has money.

–26th St & 8th Ave

Sorority girl: I’m in three exclusive relationships right now.

–uptown 1 train

Overheard by: molz

Young guy: Well, I called her a ho, but I didn't mean it.
Young girl: But she was your date!

–14th St & 7th Ave

Barbershop quarter guy: Hey, she’s walking on the outside. That means she’s available. Tell that guy you’re with that walking on the outside means you’re available.
Guy: Um, she’s my sister.

–Spring & Wooster

Russian guy: You should introduce me to your sister.
Frat guy: Hell no, man.
Russian guy: I would introduce you to my sister.
Frat guy: Dude, what do you do in your country? Meet in neutral territory and swap family members?

–23rd & 10th

Overheard by: Mariclair Partee

Woman #1: So are you still seeing that Rob guy?
Woman #2: I guess. He came over the other evening.
Woman #1: Oh, that’s good. Did you do anything fun?
Woman #2: Well, we were going to make cookies, but then I remembered I had some fish I needed to cook.

–Bistro 60