MILF

Girl: So how's your cougar?
Guy: She's good.
Girl: What is she, 50?
Guy: 52.
Girl: And you're…32?
Guy: 34.
Girl: She ever been married?
Guy: Divorced. That's how I got right in there.
Girl: So is this, like, something serious? Like a forever thing?
Guy: No! I mean, I want kids, and she keeps getting these heat flashes. You know?

–L Train

Tourist guy #1: New York is cool man, a lot of places to visit and shit.
Tourist guy #2: Yeah, I know… I can’t wait to find me one of them horny-ass "Sex in the City" whores to suck me up while I’m here.
Tourist guy #1: That’s a myth, you fag. It ain’t real.
Tourist guy #2: Look at those moms over there. I bet they’re craving some young cock.

–Outside Radio City Music Hall

Overheard by: FatCop

Teen #1 (after looking up at advert for Sex and the City): Dude, Sarah Jessica Parker is like, so freakin hot!
Teen #2: She's older than your fucking mother!
Teen #1: Which like, so totally backs up my point.

–7th St

Overheard by: Joel Moore

College guy #1: I really regret not having sex with a friend’s mom in high school. Remember Mike’s* mom?
College guy #2: She was so hot. Dude, I beat her in Monopoly… which, in my book, is far better than sex.

–14th & 7th

Woman on cell: Oh, and by the way, I called my mother to thank her. (pause) No, I said, "Mom, I'm calling on behalf of me and the girls to thank you very much." (longer pause) Well, she can just go fuck herself then.

–90th & Amsterdam Ave

Man on cell: You know a guy really likes a girl when he takes her home to meet his mom…and you know what, Sheila? You ain't never gonna meet my mom.

–South Slope, Brooklyn

Overheard by: smfd

Female college student to friend: We really need to cougarize your mom.

–111th & Broadway

Overheard by: Oh really

Guy: So, hey, my mom didn't die today.

–W 26th & 8th

Overheard by: Katie_AK

Girl sneaking into open conductor's room in front of the train: Next stop, your mother's asshole! Stand clear of the closing cheeks!

–6 Train

Overheard by: Adriana

Handbag seller on street corner: Yo! Tell yo mama I got her bag right here!

–Times Square

Overheard by: Taryn

Girl on cell: Yeah, I'm bussin' it for now, my mom's on this thing that I have to show her responsibility… I know, it's like I get up in the morning, I haven't gotten arrested in a while, and I have a job, what more do you want from me?

–Seguine Ave & Waterbury, Staten Island

Male yuppie to female yuppie: So milfs are totally in right now.

–Starbucks

Overheard by: Lolita

20-something male yuppie, surrounded with Starbucks coffee containers and yelling at laptop: It took you six fucking minutes to get to the fucking page! Rawwwr! I'm going to rip you apart, you stupid fucking computer! Rawwr!

–Starbucks

Yuppie-hipster mom, to sobbing toddler: Yeah, I know, your life is just so tough.

–Metro-North

Overheard by: It's because those hemp diapers you make her wear chafe like hell.

Yuppie woman: This is like the Third World!

–8th St & Broadway

Overheard by: Sam Chalek

Hot gay ginger: Ooh! Look at how yummy these grapes look!
Cute half-Asian: Not as yummy as that dilf outside…

–Dean & Deluca

Overheard by: reid r.

Headline by: Myrtle Willoughby

Runners-Up:
· “And So Grape Nuts Were Born” – DRS
· “How to Toss a Half-Asian Salad” – jeffreydanna@gmail.com
· “It’s Official: Gay Men Are the New Teenage Girls.” – Steve
· “Some People Just Prefer Bananas” – Hot gay ginger
· “That’s Why They Call It the Fruit Section.” – Jesse

Click here to see the new Headline Contest

Sleazy biker, taking a bottle from marathon relief table: My mother always told me I should be bottle-fed.

–Central Park

Overheard by: Uncomfortable volunteer

NYU student on cell, angrily: I was trying to show your mom a good time so I wouldn't have to stick my dick in her again!

–Washington Square Park

Overheard by: chris k.

Guido on cell: So you fucked the mother *and* the daughter?

–23rd & 3rd

Guy to girl: Anything over 50 is a super milf!

–Chelsea

Teen to friend: Cause I ain't no full-time mama. I'm a part-time mama.

–Church & Chambers

Middle aged hipster with ponytail and gray streaked goatee: I'm a soccer mom!

–Times Square

NYU guy: I was totally into Obama until we met Sarah Palin and now she has made me all Republican for her milfiness.
Friend: You know you don't get to fuck her just because you vote for her?
NYU guy: But I can only hope for my brothers in DC. You know like some Bill Clinton intern shit up in the White House, but this time with a hot mother instead of cigars and shit.

–L Train

Overheard by: Nikki

Girl: You always thought my mom was hot while we were going out. You'd be all “Oh my god, your mom is totally hot. I'd hit that.”
Guy: Well, she is!
Girl: I know that! But you can't want to fuck my mom and get all pissed when I want to fuck your sister!

–78th & Amsterdam