Manhattan

Hipster guy: Last night my girlfriend called me Caligula.
Chick: That’s really scary, ’cause he was crazy and evil. Why did she call you Caligula?
Hipster guy: I don’t know. I mean, I guess I could understand if she was talking about his big cock.

–Office, 84th & 3rd

Overheard by: da sarkastik ninja.

Girl #1: I saw this homeless girl on the street who looked our age and I felt so bad.
Girl #2: So did you give her money?
Girl #1: No, my nails were wet.

–62nd & Lexington

Lady suit: I can’t keep coming here to get my prescription filled. They’re beginning to recognize me.
Suit: So what?
Lady suit: So, what if I get in trouble?
Suit: Why would you get in trouble? You have a prescription from a doctor.
Lady suit: If you say so. Oh, shit, I forgot to put the date on this.

–Duane Reade, 89th & Columbus

Overheard by: Veronica at http://everythingisused.blogspot.com/

Girl #1: I’m funny.
Girl #2: No you’re not.
Girl #1: Yes I am. Everyone says I’m hilarious.
Girl #2: Of course they do. That’s because you aren’t pretty.

–Virgin, Union Square

Overheard by: djlindee

Man: Want to “hang out”? I have a six pack.
Girl: Uh…no. I am at work. I can’t hang out now.
Man: I am not a cop…Baby, I shouldn’t have said that. Sorry.

–43rd & 8th

Overheard by: Katie LaGreca

Guy: I like my dick with a little pussy on the side.

–3rd & Bowery

Possible paternity litigant: Paul Newman, another girl, and my mom were all having sex together right before I was born.

–6th St & 1st Ave

Queer: Is it wrong to think of my brother while I’m getting fucked in the ass?
Girl: Oh my god, I thought I was the only freak that thought that!

–Times Square

Overheard by: eavesdropper

HS girl: Man, this school is a ho!
Security guard: Yeah, and you gotta learn how to trick it right to get what you want out of it.

–Bread & Roses High, Harlem

Woman on cell: Yeah, I have to go. I’m too distracted on the phone, and I don’t trust anyone in this terminal. People are speaking Spanish behind me, if you know what I mean.

–LaGuardia

Girl #1: Ever notice how tightly girls hold onto their boyfriends when they are walking through Chelsea?
Girl #2: Right? It’s like they’re afraid he’s going to run out into traffic and get hit by a truck.

–17th & 8th