Why Some People Will Pay $20,000 For a Date

In which I find my true calling: bringing soul mates together for large sums of money

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Illustration by Mr. Bingo for TIME

There's no upside to setting people up. At best, you're stuck writing a speech for a wedding; at worst, you find out your friends cry during sex. When I found out you could get paid to set people up, however, I got a lot more interested. I asked Barbie Adler, CEO of Selective Search, to let me spend a day setting up men who pay her a minimum of $20,000 a year to set them up on dates with women who want to be set up with men who pay $20,000 a year to be set up on dates. This was the kind of love I could deliver.

I got to Barbie's office in Chicago, where I was the only man employed. All the women who interview her clients were attractive and had posters and sculptures about love in their office. This was not the tone I was going to set with my clients. I was just going to ask them if they were boob men or butt men and get to work.

But Barbie is a former executive recruiter, so she and vice president Nicole Wall gave me a 15-page form to fill out for each client that included questions about charity work, health, exercise habits and past relationships. There was another form for me to fill out after each prospective date left, and it included blank lines for items like Rate her face on a scale of 1 to 10, How is her skin?, What size do you estimate she is on top? and What size do you estimate she is on bottom? This system has led to 1,221 marriages and 417 babies; 88% of Barbie's clients meet their eventual spouse in the first nine months. These are, unbelievably, even better results than ABC's The Bachelor gets.

Normally, it would take a year of training before I got to set anyone up, and then I would spend many hours interviewing the client before combing through the 140,000 women in the company's database and reinterviewing some of them with him in mind. But I'm not normal people. In 10 hours, without a break for food, I interviewed eight women and two men. The women don't pay anything, but they aren't assured of a date, just like in the real world. To my shock, none of them seemed like gold diggers. They had great jobs, went to impressive colleges and had other priorities — namely, that they would under no circumstance date a man under 6 ft. (180 cm) tall. He could be bald, fat and jobless as long as he was at least one standard deviation above average height. It makes absolutely no sense that we're the gender that doesn't wear high heels.

Before my interviewees entered or left my office, I had to call the receptionist to run traffic control to make sure that no one else saw them. Barbie said this was done to ensure client privacy, but I think it was just so I could stop women as they went to leave and estimate how big they were on bottom. I, by the way, have no idea what scale is used to measure on bottom. I didn't know if it was just an S-M-L thing or if there was a number or if I was supposed to use terms I heard in Sir Mix-A-Lot songs. I wound up just trying to draw something.

More shocking than the non-gold-digging women, however, were the men. Who were hot. And socially well adjusted. With M bottoms. Basically, they were older guys, often divorced, who were serious about getting married and having kids and hated dating. Ironically, because of all the gold diggers. A divorced real estate developer told me, "My first reaction was, I'd never pay $20,000 for a date. Then I thought about what I normally spend $20,000 on." I was falling in love.

People were really honest. The developer said that not only did his marriage become sexless after he and his wife had children, but she refused for more than 10 years to go on vacation without the kids. He also said he liked Brazilian butts.

The next morning, I went back to the office, sure of which woman to set the developer up with. But Barbie and Nicole were positive I was going to suggest this other woman since she and the developer both had kids and she was South American with an L butt. They accused me of being attracted to the woman I was suggesting, which, while true, deeply offended my professionalism after a long day of staring at women as they walked away.

I agreed to go with their professional opinion. But I had trouble sleeping that night, thinking I was cheating two people out of true love and one person out of $20,000. Yes, the woman was missing lots of things on his wish list — like an L butt — but they had similar temperaments, shared a sense of quiet confidence, and seemed as though they would banter and go on adventures and challenge each other. Barbie was so impressed by my dedication that she said she would give my choice a shot. They've been on six dates so far. If I have to write a speech for their wedding, I'm going to be pissed.

This article originally appeared in the March 28, 2011 issue of TIME.