A Southern California-based writer has opened up about her time working as an executive assistant for a reality star once called ‘America’s Most Eligible Man,’ recalling how her main task was to organize the names, phone numbers, and sexual descriptions of the women he’d meet.
Writing for Narratively, Joanna Greenberg reflected on her time as a 19-year-old NYU sophomore who needed cash and took a gig assisting a semi-famous reality TV, personality whom she found to be ‘deeply insecure’ and ‘sad.’
Joanna did not identify her former boss by name — nor did she reveal what reality show he starred in — and simply referred to him as ‘Ben’ throughout her piece.
Story time: Southern California-based writer Joanna Greenberg wrote an essay about working as an executive assistant in NYC when she was 19
Joanna wrote that she worked for the man for two months while attending New York University 15 years ago.
She described the man as 15 years her senior — so, about 34 at the time — and said that he worked as an analyst at a prestigious financial firm.
‘He was tall, dark, and generically handsome, and he wore the same weekend uniform as all of the other similarly situated white dudes in the East Village: dark washed denim, designer T-shirts, and brown leather loafers,’ she said.
Most tellingly, he had starred on one of the first seasons of an ‘uber-popular reality dating show’ two years before they’d met.
‘He had managed to springboard his way into the glamorous world of D-list New York celebrity,’ she said, remembering how a waiter complimented him on the show while they had lunch during the job interview.
After the show aired, he had become a spokesperson for a popular dating website and ‘dreamed of a career in television’.
Joanna recalled that when she started working for him for $15 an hour, he lived in ‘a trendy building in Alphabet City, in a large loft-style apartment with four roommates.’
Her job required her to come to his apartment and organize contact information for his romantic prospects and conquests.
This involved sorting through a shoebox of ‘hundreds’ of napkins, scraps of paper, and business cards with women’s names, ages, and numbers on them.
What’s more, her boss added an evaluation to each, describing one as having ‘fake tits that felt real’, another as having a husband who traveled a lot, and yet another has giving good oral sex.
Joanna had to file all of this information into his Microsoft Outlook contacts in a ‘Black Book’ folder, a task that she says he thought she would find interesting because she, like him, is also attracted to women.
Player: Joanna said that her main job was inputting ‘hundreds’ of women’s numbers from napkins and shreds of paper into the unnamed man’s digital black book (stock image)
‘He thought that we could relate to each other based on our shared sexual attraction to women, but I did not at all relate to [his] romantic pursuits,’ she said. She found the notes misogynistic.
‘In the mornings when I arrived, Ben would casually hand me a new stack of women’s numbers and evaluations. He did this without any overt display of emotion, but in hindsight, I can remember a certain twinkle in his eyes. He seemed to want me to react, and while I tried my best not to, I have never had a poker face,’ she said.
During this time, she also read his emails, which she said made him more relatable. She learned that he genuinely thought he’d find love on TV, and would send ‘long, sad emails’ to a life coach about his ‘failure to become more famous or find a wife.’
‘He was deeply insecure and vulnerable, and he was trying to f*** his way to self-esteem,’ she wrote.
One day while they ate lunch together, he was complaining about his love life when she spoke up.
‘If you really want to get married, the way you’re going about it is silly,’ she told him. ‘Women don’t want to be objectified. You should ditch the black book and just try to be honest with someone.’
She remembered him being receptive to her advice, saying he’d discuss it with his life coach. She was amazed that it appeared to be the first time someone told him to respect women.
Considering the shoebox of names, she added: ‘It wasn’t hostile, it was sad, desperate. A man-child with no real intimacy in his life but crumpled napkins and the memories of sexual conquests.’