Dating

Girl #1 to group: Well, he doesn't have a job, or a car, and has a cat named Jedi.
Girl #2: Wait…who is this?
Girl #1: The guy I slept with last week.
Girl #2 (sarcastically): Quality!
Girl #1: Well that's why I just slept with him, instead of dated him.

–Therapy Bar

30-something woman #1: It's only a matter of time when you start dating a guy before he asks you the question.
30-something woman #2: What question?
30-something woman #1: C'mon, the thing that every guy asks for in bed.
30-something woman #2: Ooooooohhhh, anal sex.
30-something woman #1: That's the question!

–E Train to Queens

Overheard by: butt, of course

Headline by: Brian Costlow

Runners-Up:
· “Alex, I’ll Take “Things That Will Never Happen” for $100″ – The Trayster
· “Gotta Stop Meeting Boyfriends at the Pray Out The Gay Sessions.” – KJM
· “I Always Keep My Strap-on in My Purse – Just in Case.” – Sodajerk
· “I Just Hope He Doesn’t Ask at a Baseball Game. Too Cliche.” – pieski
· “Pooping the Question” – tech98
· “Reason #32 to Be a Lesbian” – Trey Jackson

Click here to see the new Headline Contest

Guy: So, tell me about this new boy.
Girl: Well, technically I’ve already slept with him.
Guy: Really?
Girl: Remember that orgy? The guy who wasn’t Richard? That was him.
Guy: You know, I wasn’t at that orgy.

–4th & Mercer

Girl #1: It’s so weird that I used to do online dating. I guess I felt like, because it was Nerve.com, it was okay, because Nerve is for the sex crazed.
Girl #2: How many people did you sleep with?
Girl #1: Eight.
Girl #2: Wait a second– do you really like sex?
Girl #1: No, not really.
Girl #2: Good, me neither.

–Bleecker & Charles

Yuppie girl #1: So he said he couldn’t date me.
Yuppie girl #2: Why?
Yuppie girl #1: He said he likes to date normal girls.
Yuppie girl #2: What?!
Yuppie girl #1: Yeah, like who likes normal girls?

–Spring St & 6th Ave

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

Guy: Why won’t you spend time with me?
Chick: Because I don’t want to date you, remember? I don’t like you.
Guy: C’mon, let’s go away for the weekend. Let’s go to St. John’s — I’ll pay.
Chick: That would make me a whore.
Guy: So, let’s go.

–Spring & Lafayette

Overheard by: S

Girl #1: …I mean, I can think of plenty better reasons why I shouldn’t date him than the fact that we’re semi-related.
Girl #2: …Um, I don’t think a better reason exists than that one.
Girl #1: You are really turning it into something that it’s not. the key word here is “semi”.
Girl #2: No! The key word here is “related“!

–Hoyt-Schermerhorn station

Dominican guy: I really like your haircut.
Brooklyn guy: Yeah, the women at work really liked it, but I never take anything they say seriously because I know how ugly I am.
Dominican guy: Yeah, I know what you mean. You know like when women say “I want to be with you,” but they really don't do that…
Brooklyn guy: Okay, this is the only thing that is going to be true of what I say from now on. Every girl I asked out has said yes, but didn't mean it.
Dominican guy: Is this a hypothetical situation?

–Harlem

Chick: You think I won’t step up and kick some nigga’s ass just because I’m a bitch? I’m bisexual. Yeah, I’m bisexual: I’m half bitch, half nigga.

–Q train

Overheard by: Reb Stu