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FRIENDS & BENEFITS

I Matched With Hollywood Men to Boost My Career

The strategy did not work out as planned.

Tootsie Haine
Published
Updated
High school notebook with doodles and Don Draper of Mad Men

Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty

Welcome to Friends and Benefits. Follow Tootsie Haine, our sex and relationships columnist, into the lives and psyches of men and women, young and old, gorgeous and tragic, divine and insane. All names and identifying details have been changed to protect the privacy of the bachelors in question.

I moved to Los Angeles at 25 and waited for someone to offer me a TV writing job. It didn’t happen.

I found work in the mailroom at a big talent agency instead. A year passed, and I was the same age as the youngest agents. Most of them had been hired right after college and worked their way up.

One exception, however, was an external hire with a streaming deal already under his belt. Assistants talked about him with incredulity. I asked a mutual friend who had been at college with him what he was like. (Was he, in fact, precocious?) She said that he was smart, hardworking, and funny.

She also told me who his girlfriend was—and let’s just say she was from a well-connected family, one in the business no less. Had this agent f---ed his way to the top?

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The Hollywood Sign on Mount Lee, overlooking Hollywood, Los Angeles, 29th October 1993

My sexual currency was slowly depleting, particularly in a place like Los Angeles, where there is no shortage of the young and the beautiful. And the hungry.

Stephen Dunn/Getty Images

To me, this possibility was more impressive than the other story, the one where he had demonstrated monstrous talent in deal-striking. This man had employed an old trick thought to be extinct in the post #MeToo era, and he was a man! But also, this was different; it was something more democratic, more aspirational. And why not?

My sexual currency was slowly depleting, particularly in a place like Los Angeles, where there is no shortage of the young and the beautiful. And the hungry.

In my imagining of it, the young agent—and the presumed simplicity of a person granting a favor to her lover—was the most spiritually and physically proximate to where I was and what I could hope for. I was inspired. Why should I be a secretary for years if there is another way?

But if that way was love, would I have the time or luck to find it?

The carnal tenor of the agency office was nil. Besides, my sexual currency was slowly depleting, particularly in a place like Los Angeles, where there is no shortage of the young and the beautiful. And the hungry.

Falling in love with someone both powerful and benevolent in Hollywood was very unlikely. If I wanted to intentionally skip the years of ego-crunching administrative work, I would likely have to begin with the f---ing and hope that love and opportunity could bloom from there.

My date’s Tinseltown connections? Dried up. Typical. But I decided to stay on.

So I went on Raya and matched with Ellis, a 40-something cinematographer with nice eyes and wavy hair. We met up at his modern townhome and talked for two hours—during which he told me he had made a career change.

His Tinseltown connections? Dried up. Typical. But I decided to stay on. We did ketamine and danced to Bollywood songs in the nude, and I realized that sex and my work could never be paired together.

Don Draper (Jon Hamm) in Season 1 of "Mad Men" wearing a gray suit in front of a chalkboard that reads, "Lucky Strike, It's Toasted"

Widely considered one of the snappiest dressers in television history, "Mad Men" protagonist Don Draper (Jon Hamm) is known for his crisp suits and meticulously combed hair.

AMC/Mad Men

Sex, and particularly sex with strangers, was the calendar equivalent of a holiday. Since getting a job in corporate Hollywood, I had felt like Don Draper: the suit, the office, and the work closing in on my life.

At Ellis’s house, I felt like Don when he rips off that suit and puts on a Hawaiian shirt: the California Don; the Don who has escaped work; the Don who treats women like travel experiences.

And I was like Don, because these experiences inspired my work. Sex had failed as the mechanism for getting work, but it had also become the work. (I didn’t get a promotion or an opportunity, but I got the writing.)

Don Draper (Jon Hamm) wears a blue Hawaiian shirt and khaki jacket in Season 6, Episode 1 of "Mad Men."

In Season 6 of "Mad Men," the formerly buttoned-up ad man lets loose. Fashion-wise, at least.

AMC/Mad Men

With Ellis, I was able to use sex as a source, but not a stepping stone.

Today’s Hollywood machine is in some ways rather pure—puritanical, even. You can bang the big-time director or the nepo-baby of a bigwig, and it will be fuel, and it will be experience, but, without love (and without talent), it will no longer be a career.

Got a question about dating, an opinion on intimacy, or a comment about Tootsie’s tales? Share your thoughts with our dating columnist at tootsie.haine@thedailybeast.com.

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