Questions

Hobo: Hey, is this a movie theater?
Woman behind counter: Yeah. What did you think it was?
Hobo: A movie theater.

–Sunshine Theaters, Houston

Overheard by: Jonathan Rosenblit

Teenage boy, making out with girlfriend: Did you know my mom and I are only 15 years apart?
Teenage girlfriend: No way, that must have been really hard.
Teenage boy: No, it's good to be a young mom.
(making out resumes)

–7 Train

Headline by: Botticus

Runners-Up:
· “I’ll Show You in 9 Months” – Sandy Paws
· “In Fact, It’s Bit Of a Family Tradition” – Traditionalist
· “Please Tell Me This Isn’t What Inspired Gilmore Girls” – katenonymous
· “Psychologists Call This “Priming”” – chuck

Click here to see the new Headline Contest

Young queer on cell, laughing: I mean, what is he going to blackmail me with?

–9th & 47th

Overheard by: wondering

Older queer to boyfriend: There's nothing like listening to Bach after having sex!

–W 72nd St, Record Store

Overheard by: I'll have to try that sometime…

(40-something gay guy is looking through a clearance rack of mismatched outerwear under sign that reads "Big and tall active bottoms")
60-something gay guy, yelling: Good luck, dahling, you're in the wrong section. Find where the big desperate bottoms are and try that!

–KMart, Penn Station

Overheard by: RoverUSA

Gay black man to whimpering toddler held by mother: Don't even start with me… Thank the Lord you ain't my kid.

–M15 Bus

Young, good looking gay guy to much older ugly boyfriend: My ex-boyfriend always bought me presents…

–86th St & Lexington

Old Jewish woman to very nervous Asian 25-year-old bride to be: Honey, I've been married 53 years. The secret to a great marriage? Give him lots of sex. Lots of good sex.

–Dumbo, Brooklyn

Overheard by: Tanya

Man on cell: I told her I would convert. We could go to Vegas and get married next week, no problem.

–64th & Amsterdam

Woman on phone: My ex-boyfriend was 24 and he was able to support me, and you're 35 on an engineer's salary and you can't do the same. Do you know how many guys are begging to marry me, and can give me a dowry? So fuck you!

–Target Store, Brooklyn

Hispanic woman on phone: So where are you now? You already married him? Oh, okay. See you later.

–28th & Park Avenue South

Overheard by: Alie

Five-year-old boy to teacher about five-year-old girl next to him: We're going to get married. (to five-year-old girl) What's your name again?

–61st & Amsterdam

Young boy: Daddy! We're going outside soon, yay!
Father: No we're not. We're going over the g line, we'll have to go to Hoyt Street underground, then switch to the f. Then we'll go outside.
Young boy: Why, daddy?
Father: Because it's the MTA.

–F Train

Overheard by: marc V

Guy: Where did everyone go?
Girl: They’re all in the bedroom looking at Nina’s breasts.
Guy: Again? Well, I guess it’s not really a party until Nina’s boobs make an appearance.
Loud girl’s voice from bedroom: Oh my god, Nina, your nipples are perfect!

–East Village

Dude: Hey, good to see you, what’s new?
Goth tranny: Oh, not much. In a new band, we’re looking for a bassist, we have a show on Saturday, my apartment sucks, Joe quit, been trying to lose weight, I need a haircut, it’s my birthday next week, and I’ve been playing World of Warcraft. What about you?

–Halloween Adventure, 11th & 4th Ave

Overheard by: Kate Melvin

Woman walking out the door to man: You smoke Newport?
Man: Sure, but what I need is a blunt, yo! (pauses, looks at woman closely) Damn, you ain't Administration for Children's Services, are you?

–Queens Family Court

Lady looking at another woman's Roman sandals: I don't like those Jesus-lookin' sandals!

–The Village

Girl: Do flats make your butt look big?

–9th St & 3rd Ave

Overheard by: Matt Morgan

Guy with faux-hawk: You know in Pee-wee's Big Adventure, after he loses his bike and everyone around him is riding bicycles? I feel that way with high-tops right now.

–14th & 1st

Overheard by: Heather

(trendy, skinny, Upper West Side woman on sidewalk is staring down at her feet and looking concerned)
Preppy 30-something boyfriend: I think your toes look better in those sandals.

–86th & Broadway

Overheard by: Sushene

Girl: My uncle is gay, like, flying-out-of-his-loafers gay.

–W 67th & Broadway

Overheard by: magical-newyork.blogspot.com

Female cop to two male cops: So he's standing there, really well dressed, nice shoes, and all of a sudden he pulls out this big, big (voice drops) boner, and says "Give me the shoes!"

–Continental Ave Station, Forest Hills

Guy to girlfriend and friend: Goddammit, neither one of you is a gay man trapped in a woman's body.

–8th & 9th

Overheard by: cracking up

Girl on cell: Are all she-males gay? Cause if they're into women, sign me up.

–Astor Place

Teen on cell: Dudes have, like, purses here…

–110th & Broadway

Overheard by: Al-master

Guy to friend: She's not a tranny, but she's, y'know: tran-y.

–Grand St & Bedford Ave

Overheard by: KateM

Man on cell: You and I are both complex women. It's more complicated than that.

–21st St & 8th Ave

Overheard by: Ben