Growing up as the daughter of meant had a childhood, unlike many others. The 33-year-old writer and director, whose mother is model , shared an insight into her unconventional upbringing, which involved spending many weekends at the infamous
Playboy Mansion, once owned by the late Hugh Hefner. "I knew the Mansion was not intended for children, but I asked no questions," she wrote in an essay for . "I never went to summer camp. I never had an after-school activity," she recalled. "From the year I was born, 1990, until I was about 11, I went to the Playboy Mansion, because that's where my
Friends were." Lorraine visited the
Los Angeles mansion with her nanny, Cis – who once worked as Hugh's social secretary – and admitted she was in constant fear of seeing something she shouldn't. "I could not have been less curious about sex or sexuality," she stated. "I was constantly vigilant, in terror of being exposed to something I wasn't supposed to see. "I never picked up an issue of Playboy, though they were left in every room. I never once questioned the original purpose of the mirrored furniture-less room in the game house – or why every bathroom had its own selection of Vaseline and tissues," she added. The filmmaker explained that former playmate Kimberley Conrad – who was married to Hugh from 1989 to 2010 – would typically watch her and her younger brother Ray, 32, as well as her and Hugh's sons, Marston, 33, and Cooper, 32, at the mansion using a security camera. Despite her frequent visits, Lorraine revealed that she "rarely stayed at the Mansion after dark," but noted it was "not because anything nefarious was going on, but because it was boring". She wrote: "The adults would jockey to sit next to Hef. The kids were pretty much ignored because we had no opinions on censorship or the hypocrisy of
American sexuality." Despite sometimes feeling out of place, Lorraine "loved everything about the Mansion," and compared it to the "magical" worlds she saw in
Disney movies, describing the people there as "one big unconventional family". One particular spot that Lorraine recalled with fondness was the grotto, an enclaved pool famous for spontaneous debauchery. "I loved the rich smell of enclosed wetness," she reminisced. "I loved the fleshy temperature of the point where the pool water met that of the hot tub. I even loved the secret tunnel that connected the grotto to the deep end." She added: "Though there was a time when I went to the Mansion every day, I never became jaded. At that time, I really believed no one could be hurt there." Lorraine and her brother Ray are two of five children Jack shares with four different
Women. He also has a sixth child, estranged daughter, Tessa Gourin, who he has never publicly acknowledged as his own. His first child, Jennifer Nicholson, 60, was born in 1963 during his marriage to Sandra Knight, his first and only wife. He has a son with his former co-star Susan Anspach, Caleb Goddard, 53, and a daughter with model Winnie Hollman, Honey Hollman, 43. In a 2010 interview with , Jack opened up about fatherhood and his close bond with Lorraine and Ray. He said: "We've always gotten along. I want to be inspirational, or some kind of good influence on them without overburdening them. It's their time of life to find out who they are."