Dating

Sketchy guy to hot girl: Hey, baby girl, I like takin' long walks through the projects, sittin' on a park bench eatin' French fries… (she walks away) Hey baby, come back!

–Christopher & 7th

Guy to girl walking down the street: Hey you…I wanna get on your bus.

–125th b/w Park & Lexington

Overheard by: Reilly

Big dude to hot girl: Hey girl, come talk to me for a minute. (she stays still) C'mon girl, chubby thugs need love too.

–Franklin Ave & Eastern Parkway, Brooklyn

Black thug to white girls: I'm Barack Obama's cousin, wanna go on a date? (they pass) That's gonna be my new pickup line, yo.

–33rd St & 6th Ave

Guy, as a curvy woman struts past him: Shake what yo momma gave you…not what yo momma paid for!

–Shuttle Train

Overheard by: Meredith

Seton Hall jock, leering at female in next seat: Wow, this ticket has more holes in it than I've ever seen before!

–NJ Transit

Drunk guy to girl on subway platform, after Yankees game: I'm a classy guy! I will take you to the fucking Radisson!

–Yankee Stadium Subway Platform

Elderly female employee, out on smoke break: So I met this gentleman at the coffee shop the other day.
More elderly woman: How do you know he was a gentleman?
Elderly female employee: I don't, but I sure hope he's not.

–CVS Pharmacy

Man on cell: Well, at least my dick will finally seem bigger!

–Prince St. & W Broadway

Overheard by: Johnny

Puerto Rican lady on phone to pal: Yo, his dick was mad little, yo! My son's dick is bigger than that!

–Broadway & Havemeyer, Brooklyn

Teen on cell: And you have a small penis. And you're gay.

–Brooklyn

Overheard by: And I Thought My Day Wasn't Going Well

Black gay guy on cell: I feel so sorry for guys with small penises. Here I am, with a 12 inch dick and I don't even use it.

–Penn Station

Man on cell: You're dumping me because my dick is 11 inches and it's too big? That doesn't make any sense!

–Lorimer & Maujer

Overheard by: was this a lame attempt to hit on me?

Petite yuppie on phone: Oh my god! It was so small I tried so hard not to laugh! But then I decided to boost his spirit and I said to him, "is it because it's cold in here?" (pause) Yeah, you're right, that couldn't have possibly boosted anything at all. Dinner was good, though.

–N Train

Overheard by: Mefisto

Teenage Asian girl: I have a question: would you want me to hang out with a vampire?
Old Hispanic woman: No!
Teenage Asian girl: Okay. I knew that.

–2 Train

Overheard by: Ryan

Big girl: Eww! I miss the days I went out with Eric.
Friend: Why? He was an asshole!
Big girl: He took me out so much, I swear I went to every cool spot in New York City.
Friend: Wait, so bascially he wined and dined you?
Big girl: Yep!
Friend: What the fuck, I thought fat girls didn't get wined and dined!

–Coffee Shop, Union Square

Girl #1: So I texted everyone and told them he was gay, but no one believed me.
Girl #2: Of course he's gay. You used to date him.

–M-15 Bus

Overheard by: peter

Young man to friend: So, about your girlfriend…I think she and I should fuck.

–Union Square West & 16th St

Street hawker selling datebooks: Wanna cheat on your husband? Plan it out! Get a daily planner, write it in red!

–Herald Square

Overheard by: MPW

Hipster teen girl to friend: Dude, don't worry about it. Whenever I want guys to cheat on their girlfriends with me I always just take off my pants and start singing Afroman.

–Mulberry St

Chick to friends: Seriously, it's a full-on dating service for married people. (pause) Like, adulterers.

–Broadway & Avenue of the Americas

Overheard by: Chuckles

Guy to another: Have you been cheating a lot? Does she know you're gay?

–6 Train

Hobo: So would all unhappily married women please step forward? I know there are some unhappily married women out there, and I'm willing to satisfy your needs. (pause) I know you're out there!

–Times Square

Overheard by: John

Chick: You rotate girlfriends like handkerchiefs.
Dude: If they are confused bitches who like making me uncomfortable.

–Roebling Tea Room, Williamsburg

Girl #1: I don't think I'll be dating anyone anytime soon.
Girl #2: But why? We'll be going to college in a few months.
Girl #1: I know, but I just don't think I can settle for anything less than an Italian R&B singer.

–77th & 3rd

Woman on date: So tell me about your trip through Asia.
Man on date: Um… Yeah, so after dinner, do you want to go to K-Mart so I can watch you buy sheets? Because it would really turn me on if I could watch you buy sheets.

–East Village