On the slopes: bachelor Sands in Aspen Photo:Zach Ornitz/Aspen Daily News

Many moments of my five-year, post-Duke lifecould be characterized as impassioned, idyllic, or inspired. This, how-ever, was no such moment. I was running through the deserted early morning streets of lower Manhattan. I was alone, mostly, except for the camera crew, sound technician, and producer strewn out on the street behind me.

Playing the Game

I was two weeks into the production of The Bachelorette, ABC's widely watched reality-television show, in which twenty-five (presumably) eligible bachelors compete for the affections of one (presumably) desirable bachelorette. The object of our affection and the star of this particular show was Jen Schefft, an attractive, twenty-eight-year-old from Chicago and a former contestant on The Bachelor (a similar reality show, except the roles are reversed). Tonight, it was Jen I was seeking as I ran through the uncharacteristically quiet streets somewhere around Little Italy. Actually, I knew where she was--thirty blocks north and eighty-five stories high, at the top of one of New York's most iconic structures, the Empire State Building. Now I just had to get there, fast.

Earlier, the show's host, Chris Harrison, had interrupted Jen's group date with me and three other bachelors at Puglio's, a famous pizzeria in Little Italy, and taken her from us to a waiting limo. (I'm regularly asked if the group dates were "awkward." In a word, Yes. I suppose we maintained our sanity by thinking of Jen as our "collective" girlfriend. At least we liked to think of her as "ours." But, more accurately, we were hers, a collection of obsequious male courtiers. It worked, as long as everybody kept his hands to himself, of course.)

When Harrison returned, he told us that she was headed to the top of the Empire State Building. We were to follow her, but, much to our dismay, there were no additional limos waiting outside. Instead, we were given the challenge of finding our own means of transportation--a race between the four bachelors on this particular date--and we had to do so without using any money or breaking any laws. The winner would enjoy some coveted one-on-one time with Jen.

And so here I was, running through the deserted streets, camera crew in tow, looking for a cab to sweet talk into a free ride uptown. The longer I ran, the more difficulty I had suppressing the only question that seemed relevant at the time: "What the hell am I doing?"

In fact, I had asked myself that question a number of times over the three months since I received the first of what would turn out to be many calls from the producers of The Bachelorette. I was living in Aspen, Colorado, when I first got their message. A passion for skiing, fishing, and biking had inspired me to leave my job at the (now-defunct) academic pop-culture magazine, Lingua Franca, in Manhattan and head to the small, opulent mountain resort community. I had been teaching skiing and tending bar to earn a living and sustain my lifestyle--not necessarily using my public-policy degree, but, as I told my parents, "just getting the 'ski-town thing' out of my system."

I was described on the show as "Ben Sands, 26, Ski Instructor," but it was bartending that had gotten me there. A few months earlier, I had won Aspen's annual bartending competition, "The Aspen Cocktail Classic." The city used the event to promote restaurants and nightlife in Aspen and, as a result, pictures of me and my creation, the "Aspen Sugar Daddy," had turned up in magazines and newspapers around the country. The producers saw the story and gave me a call--a preliminary inquiry to find out who I was, what I did and, of course, if I was single.

Single? Yes. Desperate? You'd have to be, right? Without a doubt, it's an unorthodox way to meet your future wife. Then again, one girl, twenty-five guys--it reminded me of Big Beer Thursdays at Satisfaction, the Duke student hangout. Only this time there'd be cameras, microphones, and a national television audience to capture, share, and critique your success and failure. I knew that it was a crazy idea, but when the producers invited me out to L.A. to take part in the final casting interviews, I went.