Compliments

Drunk college girl: I don’t mean to have sex with ugly guys but more often than not…

–Columbia University

Overheard by: Lo

Thuggish dude on cell: … You want to look in the mirror and be like ewww, while everyone else looks at you and is like, ooh, you know what I’m saying? When I wake up in the morning and I look in the mirror I think to myself shit, I am one ugly motherfucker, how the hell do I get so many bitches?

–7 Train

Overheard by: Andrea

Dumpy man waiting on line: I didn’t know court was a beauty contest for ugly women.

–Downtown NYC Courthouse

Man fighting with random woman on train: You’re as ugly as the tip of my dick!

–4 Train

Overheard by: Marlon B

Teenage girl to group of friends: Oh! Did I tell you *Jessica had her baby? Yeah, that shit ain’t ugly.

–Cobble Hill

Loud girl: Omigod I’m soooo pissed! Like, she’s so ugly. Much uglier than me. And you know on Halloween, if I hadn’t been bleeding from my vagina and puking in a bowl he would have hooked up with me instead.

–Fordham University

Overheard by: I was puking in a bowl when I heard this too

Drunk girl walking past man: Ohmigod, mistah, you is taaaallll! You already know that, though.
Tall man, unfazed: Thank you.

–Broadway & 151st St

Overheard by: Milton

Upper West Side girl #1: Wow! You've totally lost weight.
Upper West Side girl #2: I still eat what I want… I just eat fewer meals.
Upper West Side girl #2: So, what? You eat like one meal a day?
Upper West Side girl #1: More like one and a half.
Upper West Side girl #2: Well, you look great!

–ATM, 72nd St & Columbus

High school girl #1: Rachel*, do you really find that man attractive?
High school girl #2: His personality is perfect!
High school girl #1: He is 50 years old!
High school girl #2: So?
High school girl #3: Yeah, I second that: so what?

–Central Park

Headline by: Tom

Runners-Up:
· “His Money Doesn’t Look a Day Over 20” – Nik
· “Mr. Belding Only Got Better with Age” – RBNY
· “Now, Let’s Make a Pact to Be Impregnated by Him…” – T
· “Who Says Santa Can’t Be a Babe Magnet?” – Nael B
· “You Might Want to Check the Expiration Date on That Personality” – kenderbard

Click here to see the new Headline Contest

Fat queer to lady with baby in carrier: Oooh! That’s the kind of job I want. Get carried around all day and sleep whenever you want!
Baby daddy: Yeah! And suck on boobies all day!
Fat queer: Ewww!

–York St station

Wasted guy: Hi.
Cute girl: Hi.
Wasted guy: What are you doing? You look hot bending over like that.
Girl: Um, well, I'm looking for my jacket.
Wasted guy: Huh! I have a better idea. (slight pause) Why don't you come home with me and sit on my face?
(long, long, shocked pause)
Girl: You know what… you find my jacket, and then we'll talk about it.

–Tin Lizzie, Upper East Side

Overheard by: tinajane

Woman: Have you ever been to Chelsea piers?
Man: No, I can’t say I have.
Woman: Oh. It’s wonderful. It has a great view of New Jersey.
Man: (sounding disgusted) Oh. (feigning interest) New Jersey, huh?

–Elevator, 25th & 8th

Guy: How was the weekend? Were the kids well-behaved?
Woman: It was fine, they were great.
Guy: How was Max at night? He sometimes gets lonely and starts crying.
Woman: Hmm, I don’t know. I locked them out of my room.
Guy, yelling: You what?!? How could you? You know how they are at night!
[pause.]Woman, unruffled: They are pets. Not kids. Pets. And I don’t sleep with dogs that weigh more than I do.

–Starbucks, 20th St & 6th Ave

Old man wearing suspenders #1: That's a great pair of suspenders.
Old man wearing suspenders #2: Thanks. I had a heckuva time getting them.
Library security guard: Sir, please lower your voice.

–New York Public Library, 34th & Madison

Stranger: Hey, big dick!
Black guy: Hey, what's up guy. Not big dick anymore, small dick! (motions with hand)
Stranger: Not what that girl told me last night, haha.
Black guy: Well, alright, take care.

–Union Square

Overheard by: Brandon