Content Warning: This section discusses women’s objectification, sex work, sexual intercourse, substance abuse, and suicidal ideation.

“And while I am grateful, it’s also clear to me that most people fail to realize that there are two sides to every coin and that even the most fantastic fairy tale has a dark underbelly. Being attached to Playboy can make people not want to have anything to do with you, even in quirky, crazy Hollywood. There were many times the hateful backlash made me wish I stayed the broke, awkward 21-year-old waitress I’ve been before Hef came into my life.”

Holly points out that the intentionally projected facade of the Playboy lifestyle was not what it appeared. While it may have appeared to be a dream-like fairy tale on the surface, in reality it was painful and incredibly challenging. She experienced a great deal of backlash from those prejudiced against her integral involvement in Hefner’s world. Her underlying ambition, springing from the paucity of her life before she entered the mansion, shines through as the underlying reason for her willingness, even eagerness, to be part of Hefner’s world.

“I had to believe that there was a greater purpose for the choices I had made: whether it was to help advance my career or whether it was truly for love. And depending upon the month, the week, and sometimes even the hour of the day, I would waffle back and forth between precisely why I was living a life as nothing more than ‘Girlfriend Number One’ to a man who was old enough to be my grandfather. I didn’t want to admit that I had sold a bit of my soul for the chance at fame.”

Holly reflects on a period when, early during her stay in a mansion, she was suicidal. As the girlfriend who slept with Hefner in his bedroom each night, whom he boasted was his one true love, Holly realizes that she has reached the height of what life with Hefner has to offer her. She asks herself what legitimate reason she might have for remaining in this setting. Although it offers her luxury, extravagance, and a modicum of fame, it restricts her possibilities and outside activities.