Dating

16-year-old girl to friend: Halfway through the date he took out a puppet and started singing.
Excited friend: Really? Oh my god, he is husband material!

–Union Square

Overheard by: Justin

Buff 20-something black guy: Yeah, she was that one I was going out with last summer.
Tall 30-something black guy: So what happened?
Buff younger black guy: She got fat! In like two weeks! And also, she was cheating on me: she never told me she hadn't broken up with her boyfriend at the time!

–Planet Sushi, Amsterdam Ave

Overheard by: Susan Volchok

Teen girl: Anna told me you liked me?
Teen guy: Yeah.
Teen girl: Why didn't you tell me or ask me out?
Teen guy: Well, I was afraid you would say no.
Teen girl: Why don't you ask me now and see what I say?
Teen guy: Do you want to go out sometime?
Teen girl: Sorry, no.

–Starbucks

Overheard by: Hugh

Girl #1: So how was the movie date with Adam?
Girl #2: Good! We saw Watchmen. I really liked it!
Girl #1: Did he like it?
Girl #2: Yeah, but he was upset about the nudity. The cock-to-tits ratio was not in his favor.

–58th & 8th

Puzzled guy on cell: What kind of girl calls you a "cuddly wuddly bear" and doesn't go out with you?

–The Village

Overheard by: Greene

Hobo: Hey there, folks! I'm Yogi Bear! Have you seen Ranger Rick?

–Gray's Papaya

Overheard by: Zach

Woman on cell: I'm glad the evil bear didn't kill you in your sleep!

–113th & Broadway

Overheard by: Ladle

Drunk girl to sober companion: Oh my god, I saw this dog the other day. It was a bear!

–Tick-Tock Diner

Outraged girl on cell: She's anti-polar bear?

–NYU Campus

Overheard by: nina

Preteen boy #1: My new girlfriend told me to meet her there after school.
Preteen boy #2: Why don't you just call her and tell her you'll be late?
Preteen boy #1: I don't have her number.
Preteen boy #2: How is she your girlfriend if you don't even have her phone number?
Preteen boy #1: Cause I kissed her on the lips and she liked it!

–L Train

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