Men

Middle-Aged man: I hope we don’t get caught.
Prostitute: Don’t worry, I never have.

–81st & Amsterdam
Headline by: Sean

Runners-Up:
· “…Not Once in My Ten Years on the Force.” – Ingwall
· “Any Extra Charge For the Lip Service?” – Hobo Whisperer
· “He Was Looking For, ”Cause Then We’d Have to Be Punished…'” – alex
· “I’ve Got My Lucky Condom” – Sheri
· “Is Hugh Grant Considered ‘Middle-Aged’?” – Matthew McGuirl
· “My Parents Will Be Home in an Hour” – Lois
· “Skip the Condom. She’s Been Tested, Too” – Andy Adelewitz
· “Take Your Father to Work Day” – Sean Mc Grath

Honorable mentions:
· “Charge Me If You Can” – petch
· “If You Can’t Beat ‘Em (in Public)” – Heather
· “They Were Talking About Their Braces.” – Allison

Click here to see the new Headline Contest

Teen girl to sailor in uniform: Can you do me a huge favor and let me kiss you?
Sailor: Man, you're really twisting my arm huh?

–Top of Empire State Building

Hobo #1: I love you.
Hobo #2: Get the fuck out of here.
Hobo #1: What?
Hobo #2: You are going to fuck with me and you are going to get yourself hurt. I mean it!

–Penn Station

Overheard by: bebe

Homeless man to group of people: Excuse me, do you have any spare change?
Humanitarian: No, but here are some cookies.
Homeless man: I’m a vegetarian.

–W 57th & 8th Ave

Overheard by: Chris

Man #1, sounding exasperated: Some women are so beautiful that I can't–I just can't even look at them.
Man #2: I know. Beauty hurts.

–14th St & 3rd Ave

Overheard by: Evan

Man on date: I probably shouldn't tell you this, but since I was little I had an imaginary friend named Picoletto.
Woman he's dating: Holy shit! You know Pico!

–McDonald's, Times Square

Overheard by: JP

Chick (walking in elevator and looking at others): Sorry for staring, but you all have blue eyes.
Blue-eyed woman: Yeah, we're all related.
Chick: Really?
Blue-eyed woman: Uh, no.
Blue-eyed man: But don't worry, we'll be nice to you when we take over.

–Elevator, Roosevelt Hospital

Female day-drinking tourist: Oh shit, I left my vodka in the church!

–Outside Trinity Church

Man on cell: If it's possible to ferment it, we have fermented it.

–7th St b/w 2nd & 3rd Ave

Middle-aged man to younger man: You know how cats and dogs–they eat and then they go? In one end and out the other. I'm like that. My bladder has room for the equivalent of one good cocktail.

–10th Ave and W 50th St

Overheard by: Ah….middle age

Commuter at 8 am: Beer. Beer.

–Grand Central

Overheard by: baconista

Old drunk walking into a liquor store, to clerk: Have you got my prescription?

–Broadway & 106th St

Overheard by: rickbruner

Short, fat, toothless-sounding woman: What we do is not disgraceful. There's nothing disgraceful about you.
Tall thin man, with boom box in hand: No.
Short, fat, toothless-sounding woman: There's nothing disgraceful about me.
Tall thin man: No.
Short, fat, toothless-sounding woman: It's the sin that's disgraceful. Us, holding hands, how we show our love, that's fine. It would be a whole different story if I wasn't married, but I am.

–Essex & Delancey

Overheard by: nb

Comedy club promoter: Hey, you guys want free beers and some laughs?
Teen tourists’ chaperone: They’re underage.
Comedy club promoter: How about free sodas and a few giggles?

–Outside Hilton Theatre

Overheard by: Amused Teenage Tourist