Dating

Mom: You should find a nice girl to settle down with! Why don't you ask that girl you work with to dinner sometime?
Smartass teen: Because she's in her 70s.

–Serendipity's

Asian girl: He's the kind of guy who sits at home drinking beer, plotting ways to date his cousins.
Friend: Well, maybe that's acceptable where he comes from. Isn't he from another country?
Asian girl: Jersey.

–22nd & 23rd

Overheard by: jack

Comedy guy promoter to young JAP: Comedy show! Comedy show! Hey, do you like comedy?
Young JAP: Um… no.
Comedy guy: Come on, they're funny… just come!
Young JAP: Umm… no.
Comedy guy: Fine, don't come. But do you like tall skinny white men? Wanna go on a date?
Young JAP: Again: umm… no.

–14th St & Broadway

Headline by: Kelly Combs

Runners-Up:
· “Feigned Hesitation Is the Cruelest Of the Sarcastic Arts” – Aaron
· “How About Puppies? Everyone Likes Puppies!” – CJ
· “JAP Has No Sense Of Humor, Film at 11” – samson
· “She Actually Just Has a Rare Form Of Tourettes…” – Molly
· “What About Money?! I Bet You Like That!” – Zak Santucci

Click here to see the new Headline Contest

Girl #1: Do you think you'll go on another date with him?
Girl #2: Yeah, I'm like addicted to hobbits!

–W 20th St & 6th Ave

Brunette: I would never date a guy who wears skinny jeans.
Blonde: What's wrong with skinny jeans?
Brunette: It means he's got fashion sense. I just don't need that. I would also never date a guy who's sociable.

–Downtown 1 Train

Overheard by: wearing skinny jeans and wouldn't date her either

Tired thug teen, wistfully: I'd dance like crazy in a basement.

–R Train

Overheard by: Jon A.

Two-year-old boy, pointing at three-month old baby: Isn't that guy in my dance class?

–Red Hook, Brooklyn

Overheard by: Swimfan

Clueless man to friend: What do you call male ballerinas anyway? Ballers?

–Cirque du Soleil Show, Randall's Island

Overheard by: TheGreenCat

Girl to friend: I didn't dance with him at all…I kept walking away from him…I wasn't actually a very good prom date.

–Bronx Zoo

Overheard by: wink

Metrosexual on cell: Do you have a large table in your apartment? Is it large enough for five men to stand on? Of course, we won't be dancing!

–Upper West Side

Female undergrad #1: How was your first date with that new guy?
Female undergrad #2: Really great! I must really like him, because I didn't sleep with him.

–NYU

Drunk girl on phone: Yeah, so I decided that I'll go on a date with you. (pause) Well, I made out with some guy tonight and… (pause) No, I don't think he's cuter than you. He's not really cute at all!
Guy she made out with: Um, I'm right here.
Drunk girl: Shhhhhhhhhh, I'm setting up a date with a cute guy!

–1st Ave & 8th St

Overheard by: amused

20-something girl to two girlfriends: We've been dating for two months. Normally in my relationships, it's "he loves me, and I love me," but now I feel like he knows I like him, and that threatens me.

–Penn Station

8th grade boy to another: Aren't I the woman in this relationship?

–Bell Academy

Woman to friend: He said he wanted to dress me up, take me out, and show me off to the world. Instead we'd go out, he'd make me pay, and tell me how great everyone else looked.

–3rd Ave & 37th th

Cute guy in Yankees hat: I need a wild, destructive relationship for awhile.

–Brother Jimmy's, 81st & Amsterdam

Guy: Yeah, I just got over a long-term relationship. You know, two to three months.

–Starbucks, 67 & Columbus

Guy on cell: I don't know if I already told you this, but I don't have a job or a show. So we could go a date until the end of time.

–MacDougal & 7th St

Steve Guttenberg to way-too-young date: I like you and I would like to see you, just not every day.

–Upper West Side

Suit on cell: I mean, imagine our mothers in Playboy

–Borders, Penn Station

Overheard by: I'd Rather Not

50-something suit to others: Ya, we sold ten bags of herb and made $100.

–Wall St & William St

Overheard by: Mike D

Suit on cell: Hey, mom! Ma! 7 cents! You owe me 7 cents!

–5th Ave & 22nd St

Overheard by: Katie

30-something suit to hot female: I can't reassure you about your body while we're in bed, because that would imply that there's something going on between us.

–W Broadway & Houston

Man in suit: Every day I try to do something out of my comfort zone, like hanging out with you.

–Broadway & Murray St