I recieved a "solicitation card" similar to the one featured on Gawker today a few years ago. I was approached in the 51st street subway station by a man who I assumed was going to ask for directions but instead handed me this business card and walked away. The card's background was a picture of a beach at sunset and introduced him as Arthur and explained that he was handing the cards out to people he wanted to be "friends" with and included his contact number. Wish I still had it, I'd send a picture. Apparently Arthur isn't the only one out there looking for "friends"
Midtown, again:

Hi, this happened to me about six months ago...I got on the 4 train at 59th Street heading downtown, exhausted from a day in the professional clutches of "The Man," and a shortish brown-haired dude in a bomber jacket offered me a seat. I declined mainly because I was startled; I wound up standing next to him for the rest of the ride. I shut my eyes and hung onto the bar for most of it, and when we got to Bowling Green he tapped me on the shoulder and handed me a card emblazoned with "We'll Laugh About This a Year From Now" and a URL below. I promptly freaked out and figured that while I was nodding off he put together some subway upskirt video (In retrospect pretty unlikely as youngish professional women aren't typically the target audience for that, particularly if it's THEIR ladybits on view). Upon googling the URL I discovered it was some kind of matchmaking service that gives the perpetually shy and/or gutless a batch of "funny" cards so they can reach out to people without having to say anything.

I was pretty creeped out by it — even though the guy meant no harm. Maybe if the card had a different message? Alas, my bomber-jacketed swain and I probs won't get the chance to find out.
A wandering millionaire strikes:

I was a college student, and I used to walk to the Herald Square area from Grand Central in the early morning.

I think this guy had been scoping me because I had seen him in the area before. One day, he fell into step with me and asked me where I was going.

I told him I was going to school (my naïveté was still intact. Unbelievably, I even told him where I went to school). and he told me that if I left with him right there I would never have to work or go to school if I became his mistress.

He tried to show me his watch and clothes and urgently tried to make me go with him, saying he was a millionaire. Finally I realized how ridiculous this was and told him to leave me alone.

I felt dirty afterwards, thinking that maybe the way I dressed gave the wrong signals, though now I realize I did nothing to bring it on. Creepy men don't need provocation.
The most romantic STD clinic story of all time:

I saw your post on Gawker, and thought I'd add my story. It took place in Chicago, not New York, but I still think it's fun/strange enough to count.

In Chicago back in the day the Howard Brown Memorial Clinic was where all the gays would go to get checked out for AIDS/STDs, etc. We used to fondly call it the Clap Shack. One time in 1996 I went there for my yearly check-up. I had a long, but otherwise routine, interview with the intake guy, who seemed quite normal and even a little bored with the whole thing. He wass kind of nebbishy looking, nothing special, so I hardly noticed him.

So I had all my test fluids/swabs taken, and leave. A week later I opened my mail box and found a letter...from the Howard Brown Memorial Clinic. I almost fainted. This is one thing you definitely never want to see in your Chicago mailbox. OMFG, I thought. I'm dead. Or dying. I waited till I was inside, with a drink in my hand, to open it up and read it. Steeled for an encounter with mortality, instead I found a hand-written love letter from the intake attendant. Its opening words are still burned into my brain. "You know, I really thought we made a connection when I was interviewing you, and I was wondering if you were interested in getting together...". The relief of this was so strong it nullifed any outrage I might otherwise have felt. Then I burst out laughing, because I realized he would certainly have waited until he saw my test results before writing that letter. So all's well that ends well after all.
Super Sad True Love Stories: Unsolicited Solicitations
The following tale was sent with a photo of this note attached—we've removed the woman's name, address, and phone number, which was written on top of the note.
[img]http://i.kinja-img.com/gawker-media/image/upload/s--dDuA5WNh--/c_fit,fl_progressive,q_80,w_320/18k1w82mhhx43jpg.jpg[/img]