Would you pay someone to go out with you? On a platonic date?

A new website, Rent a Friend, charges friendless folks $24.95 per month to peruse its 100,000-plus members, who are all ready to accompany you to the movies, on bike rides, for dinner -- anywhere you can devise, really.

Of course, it doesn't stop there. Once you find a member willing to play ball, you'll still need to pay him or her a service fee -- sometimes as much as $100 an hour.

Still, as Asylum's resident investigative reporter / creepy guy with no friends, this seemed like a small price for a unique afternoon.

I had my doubts. For instance, why would anyone besides rich stockbrokers looking to hire hot models to convince their parents of their straightness ever need this site?

But a quick survey of Rent a Friend profiles revealed that most activity partners offer themselves up as tour guides, good listeners, drinking buddies and even wingmen or wingwomen. It's understandable that sometimes these roles are too difficult or too embarrassing to ask our real friends to fill, especially if you drink Amstel Light.

So I decided to try out the site, as crazy as it seemed. Keep reading to see what happened when I took a married middle-aged man out for a drink.

As in Life, There Are Plenty of Flakes on Rent a Friend

After signing up for Rent a Friend, I contacted and spoke with a punk-rock girl about hitting some dive bars, a guy from Staten Island who could show me the two or three interesting things in that hellhole, and a guy who lived in my area for more than 20 years and could show me everything there was to know about the neighborhood. None of these people seemed serious enough to warrant hiring. "Rent a Friend's great for people who are new to the city," said one user we'll call Al. "Some people need to get over that hump of not knowing anybody, and therefore not being able to meet anybody." Al, too, flaked out on our friend date.

In order to best recreate an environment most Rent a Friend clients would find themselves involved in, I decided to find a businessman who would know the Wall Street area of Manhattan, a part of the city I'd always been intrigued by because of its rich history but had always avoided because, you know, it sucks donkey balls. Joshua Persky, a financial engineer and business valuation specialist, understood my misgivings about the Financial District and suggested we grab a beer at the Stone Street Tavern, an unpretentious watering hole with outdoor seating, hidden off the path beaten by $800 Ferragamo shoes.

The First (Friend) Date

"I'm not a tour guide," Persky quickly explained, "but I do have my spots. Every square inch of Central Park. This street -- I worked near here for a year. Fraunces Tavern is right around the corner, where George Washington held court. It's still a restaurant and museum." I had no idea George Washington was such a New York City presence -- the original Bill Clinton, literally.

We settled into the first beer and immediately realized we shared several strange commonalities. For one, we both moved to the city on the same day, the Sunday before 9/11. For another, he's helping raise post-production funds for a movie some casual friends of mine just finished shooting. It also became clear that I'd heard of him -- he's known as the Sign Board Guy, who received major national press two years ago for standing around with a sandwich board that read: "Experienced MIT Grad for Hire," along with his phone number and email.

"I didn't get a job from it," he says. However, he did get a book deal and his blog on the experience eventually led to a full-time gig. Now, he works for himself, raising capital and working investment banking deals, and has time to hang out with me during daylight hours ... for $50-100 an hour, of course.

At Home, He's a Tourist

After pounding our Sam Adams drafts (hey, it was a Revolutionary War–themed evening, OK?), Persky took me on a walking tour of the area, passing quite a few sights I pretend not to know of already -- for the sake of the story, of course. We hit Fraunces Tavern, which is closed in both restaurant and museum form for renovations, but we worked our psychological powers on the doorman, who allowed us to poke around and take a few photos.

I can imagine a tourist coming over from Italy or someplace and being thrilled to have a one-on-one with a paid guide who knows the best bars and museums, the right wine to get with dinner tonight (Gato Negro from Chile), and shortcuts to cover them all in the allotted time.

All in all, the experience taught me that Rent a Friend is rewarding if you have a need for it, which most people don't, or an enjoyable and expensive diversion if you're traveling -- or well-heeled.

Back at Stone Street, Persky's cell phone buzzes with a call from his wife, who does not approve of his self-promotional side gigs. "I'm good," he tells her. "I'm just sitting here with a friend, having a beer."