My Secret Life as a Personal Assistant to 'America’s Most Eligible Man'

He was the former star of an uber-popular reality dating show. I was a feminist lesbian 19-year-old—a.k.a. the least likely person on Earth to become his coach in life and love.

Illustrations by Abelle Hayford | Story edited by Naomi Zeveloff

The first time I met Ben, I had no idea who he was. This is probably why he hired me to be his executive assistant, although he told me it was because I had “really nailed” the cover letter.

“A good cover letter opens doors. Are you considering a career in business?” he asked me at my interview, which we conducted over French toast and coffee at a little cafe on Avenue A and East 6th Street. I was grateful for the free meal. I was a sophomore at New York University, and I’d applied to the job less out of an interest in being an executive assistant than out of despair over my constantly overdrawn checking account.

“Oh, no, definitely not business,” I said, with the casual confidence of someone too young to know to lie during job interviews. “I’m going to be a poet.”

Ben, whose name I have changed here to protect his privacy, was 15 years my senior, but he kindly refrained from pointing out that I was getting a very expensive …