Men

Old grimy man to cute young bartender: Will you marry me?
Bartender: No!
Old man: I'll pay you.
Bartender: How much?
Old man: $30,000.
Bartender: Ummm… No, I would need at least 3 million.
Old man (shaking his head and talking to himself): I don't get it. It's just not fair. $30,000 is a lot of money.

–Cobblestones Pub

Overheard by: kapnasty

Headline by: hearer

Runners-Up:
· “From the Pilot for “X-Rated Price Is Right”” – BobBugger
· “Just Go Home, Mr. Hefner.” – playgeezer
· “The Market Ain’t What It Used to Be” – Rob
· “Well If You Won’t Marry Me, Will You at Least Be My Running Mate?” – Michelle
· “When Did Heather Mills Start Bartending?” – Paul Ferris

Click here to see the new Headline Contest

Skater boy: I love Jennifer Aniston! I would fuck her and then leave her!

–Uptown 1 Train

Overheard by: Laura

Grad student: I've been analyzing my love life from a symbolic interactionist perspective…

–Amsterdam Cafe

Overheard by: Ladle

Guy on cell: I love you…(defensively) Yes I do!

–Columbus Circle

Loud guy: You know what? Sometimes you've got to catch a few venereal diseases to find true love.

–Yankee Stadium

Overheard by: Kelsey

Man on cell: Then I thought that if I asked her out she would think that I think that she thinks that I think that she loves me.

–59th St & 8th Ave

Black girl behind the counter (after receiving a few text messages and calls): Why is everyone harassing me today? (sighs) I feel loved.

–Coldstone Creamery

Overheard by: Eli

Bus driver on loudspeaker: This bus is beautiful. We care about one another, we share our experiences, our dreams and aspirations. I love each and every one of y'all. So…that's what this is.

–X30 Bus

Overheard by: i just like him as a friend…

Angry man on cell: I need a friend in my life! Do you hear me?! …I don't care! I'm not leaving my wife for anyone!

–Roosevelt Ave, Flushing

Overheard by: oh, you thought my ipod was on

Girl to friend: Tomorrow I'm finally unpacking and I'm buying a new sundress to wear on Sunday when I go out to brunch with my new love interest. But he doesn't know that's the direction our friendship is headed.

–Starbucks

Overheard by: A. Pincus

Older woman with teased black hair on cell: But Frank, I don't want you to write a song about me. I want things to be as they were, friends when we were normal. Don't write me a song.

–Staten Island Ferry

Girl to friend: Well, I'm friends with him too and I didn't sleep with him.

–Shake Shack, Union Square

Girl to friend: I'm willing to let you sleep with my best friend and you still want more?

–W 31 & 6th

Overheard by: misery

Angry woman on cell: And then he told this complete stranger, "My ex-wife had lesbian lovers! My ex-wife slept with young boys!" We've been divorced for six years and he's still talking shit about me, but he says he wants to be friends?!

–2nd St & Ave A

Overheard by: voidoid

Man: Yo mama, what you readin'?
College girl: Jazz, by Toni Morrison.
Man: Oh that's cool. What's it about?
College girl: Music.
Man: What kind of music? Is that about opera and shit?
College girl: Ummm…

–E Train

Overheard by: Is that like Britney's music?

Man #1: How about Jack the Horse?
Man #2: Jack the horse. Wait, Jack the Horse?
Man #1: Uhhhh…
Man #2: Jack like the verb? No way dude, not eating there.

–Jack the Horse Restaurant, Brooklyn Heights

Overheard by: avoid the hollandaise sauce

African American man: Seeing someone get laid out on the street is a real New York City stereotype. Like if you flew to Texas and you got picked up by a cowboy on a horse.
African American woman: More like if the plane was a pickup truck and you get dragged behind it.

–Q74 Bus

Man #1: You have kids?
Man #2: Yeah, four sons. All boys.

–Penn Station

Man #1: Yes you did!
Man #2: I didn't fuck your grandma!

–Central Park Zoo

Conductor: This is the train from Grand Central to North White Plains. Next stop is Botanic Gardens. We do not go to Canada. Next stop is Botanic Gardens.

–Metro-North Train

Guy with heavy Brooklyn accent: I don't want to go to a place like Canada if I don't know where it is!

–Avenue of the Americas

Overheard by: Mike

20-something preppy boy (yelling into his phone): It's not racist to hate Canadians! Canadians are not a race!

–8th St & 6th Ave

Man on cell: What? He jumped off a bridge? You have to be Canadian to jump off a bridge!

–Times Square

Tourist: Man, I'm way too Canadian for this escalator.

–Grand Central Station

Overheard by: escal-eh?-tor

20-something woman: Why do I have a phone number for "Shrek" in my phone?

–1 Train

Overheard by: Poogins

Older, bald man on phone: Mom! I told you, you don't have to call me everyday. Just call me once a month…to see if I'm alive!

–Times Square

40-something suit on cell: You know what would be fine, mom? If you just stopped calling. That'd be fine! Just fine! Of course I want to hear from you, but just stop calling. It's over. Over. Don't call no more.

–Park Slope, Brooklyn

Overheard by: Oedipus

Crazy lady on cell (at the top of her lungs): Yo, douchebag! Where are my fucking children? I want to see my children. You owe my $10,000 in child support. And you know what? They're not even your kids! Ha! Oh, and my phone's dead.

–AirTrain

White girl on phone: Well, on the phone he doesn't even sound black. So just introduce him to your parents over the phone…

–28th & Broadway

Overheard by: Vanessa

Lunching lady: She's 718, acts like she's 212…but really, she's so 516!

–4 Train

Overheard by: JC