I don’t think you really know that you have a paid friend until one leaves your employ. At least, that was the case with my losing Lauren, who had been my personal assistant, then my development executive and also a producer with me on two TV series. When Lauren recently told me that she had accepted another job, my reaction wasn’t “Oh, shit, whom can I hire to fill her position?” It was more like “Oh, shit, my friend is breaking up with me.” While she was working for me, I would confide in her and seek her advice about my romantic relationships, listen to her when she would tell me I was overreacting to some slight by some network executive, and walk my dog with her and her dog on Saturday afternoons. I gave her dating advice and learned about her family and friends. I put Lauren in my will as the person who would get custody of my pets.
While I’m sure that paid friends exist in many walks of life, I doubt they are as common anywhere else as they are in the entertainment industry. I’ve encountered many big-deal stars and directors with an entourage of assistants and development executives who have crossed the business-personal line. Some were friends before they were employees. Others drifted the other direction. Doll & Em, the recent HBO show that’s built around a paid friendship, reflects the perceived normalcy of such relationships by those in this industry. It is such a prevalent aspect of Hollywood life that it almost feels natural—although the most salient characteristic of paid friendships is that they’re not natural at all.
The reasons paid friends exist are simple enough. It’s isolating being famous or powerful. Many of the people you would otherwise naturally like are trying to get you to do them a favor, or increase their status through association with you, so it becomes difficult to trust them or enjoy their company. You fall out of the practice of cultivating friendships; the larger your fame, the smaller your world becomes. Things are clearer with friends who are on your payroll. From the payee’s perspective, there is the obvious validation about being important to someone who is important. Some might be looking to score financially through the connection, but most respected their prospective employer in the first place and welcome the chance for a more personal relationship. For these reasons, it has become an accepted part of Hollywood culture to have an entourage. And when other important people have entourages, you want one, too.
I am not a star of any kind, so I never applied the same lens to my relationship with Lauren, but when she left I started to wonder whether our friendship was phony. At the beginning of my career, I was a paid friend myself. I had known my first boss before working as her assistant at a talent agency, and she always treated me like a friend. I hung out at her house, knew her son, and heard all of her stories about past love affairs. She would get migraines, and I would have to drive her to the emergency room to get a shot of Demerol. I also probably slacked off at my duties a bit, thinking I could get away with it because she didn’t treat me like an employee. But even though my boss would tell me about confidential stuff going on at the company and in her personal life, and seek my opinion on much of it, there was an obvious power imbalance: I never said anything about her obvious drug-and-alcohol problem or bad work habits. Delivering a difficult but necessary message wasn’t my job, and I wasn’t really her friend.
Recently, I talked to a couple of people I know who were also once on the payee side of a friendship. One, I’ll call her Jill, was in her mid-20s when she was invited by a director to become his assistant. He explained that this would give her the chance to grow into becoming a producer on his projects, which was appealing. The relationship started out as a typical assistant-boss thing, until the director broke up with his girlfriend, at which point they became closer. “We would talk about our lives. He knew about my roommates, my dating life, my family,” Jill says. “He was smart and would ask for my opinions on his projects; he invited me to screenings and concerts but was never inappropriate. We went around the world on productions and would be in his hotel room smoking pot, and he never even made a move. That was really important.” Clearly, both parties in this exchange received something they wanted: the director, companionship; Jill, a sense of influence. “I felt like he needed me,” she says.
Then the director got back together with his girlfriend, who didn’t like how close Jill and he had become. He started to make sure Jill and the girlfriend were kept apart. One day he said, “I want you to be a producer on all my projects from now on.” Jill was excited at first, asking which project she should start on. It quickly became clear there weren’t any projects. “I asked him who would take care of his day-to-day assistant stuff, and he said, ‘I don’t know, but it can’t be you.’ I asked, ‘What’s really going on?’ He said, ‘You know I love you, but I can’t have you working for me anymore.’ It was the girlfriend.” Then Jill was unexpectedly terminated by another producer on a movie. “I put in five years,” she says. “And he didn’t even stick to his word about helping me look for something else. He just stopped caring completely. It was like a big hole where the friendship used to be. I gave up a lot of my personal life, and I thought we were friends, and in the end he really screwed me over.”
Then there’s Jenn (not her real name either), who was offered the job of assistant to a huge TV star by the star’s husband. “We just really connected, and she didn’t connect with many people. She respected what I had to say. We’d go to lunch, to the movies, to get our nails done. I thought, Oh, this is how celebrities live. It was 24 hours a day, seven days a week. Then the husband suggested that I move into a room in their house, which was stupid because I already had no life and that made it worse. But I liked her a lot. When she wasn’t in front of the cameras, she was really nice and really kind. I knew her secrets, and she knew my secrets. She had become the closest thing to me.”
The problems came when the husband was around. “He was not nice to her,” Jenn says. “They would fight horribly, and she’d come in my room and want to sleep in bed with me. At the time, I felt like I was just helping my friend. And this went on for two and a half years.” Then Jenn learned that her boss’s husband was having an affair with his assistant. “I told her, and she didn’t believe me. She told her husband, but he denied it. He convinced her that I was lying because I was jealous. She got angry with me and then he fired me. I tried to reach out to [the star] over and over, but no one would let me talk to her. I was so hurt because not only had I lost my best friend but I lost my life.”
Paid friendships are tricky even without a jealous spouse, and they usually end at the discretion of the employer. But when they don’t, they reveal the dependency and insecurity built into both sides of the relationship. The employee never knows when she’ll be fired, but the employer never knows whether their relationship is ever emotionally real. When a friendship that started contractually now feels organic and genuine, is it—or is the paid friend just getting better at her job? Would the friendship survive without a paycheck?
A real friend has to be allowed to confront you with an uncomfortable truth without fearing she’ll lose her job. I always felt that this was true with Lauren, but did she? I decided to ask her. “There was a point where I didn’t think you considered me a friend, I was just an employee,” she told me. “I remember being a little surprised and then flattered when I learned I had crossed over and broken down your barrier. But after that, I would say anything to you that I would say to any of my other friends.” This made me feel somewhat better and encouraged about getting to a new, potentially more balanced, chapter in our relationship. Then she speculated on whether our friendship would continue. “I never thought you were that fickle with people, but I worry that I will be out of sight, out of mind,” she said. I guess that is something we’ll have to talk about this Saturday when we walk our dogs together.
*This article appeared in the May 5, 2014 issue of New York Magazine.