Holly Madison is opening up again about her years living at the Playboy Mansion and her complicated relationship with Hugh Hefner. Madison, who dated Hefner from the early 2000s until 2008, has previously described the mansion lifestyle as very different from the glamorous image presented to the public.

During interviews, Madison has spoken about the group sexual encounters that took place at the mansion, saying she found those experiences particularly uncomfortable and strongly disliked participating in them. She has also discussed the emotional pressure and complicated power dynamics surrounding her relationship with Hefner, explaining that she often felt he controlled much of life inside the mansion.

Madison’s experiences have been echoed in different ways by other women who spent time with Hefner. Crystal Hefner, his third wife, later described her own experiences in her memoir, while former girlfriends including Bridget Marquardt and Kendra Wilkinson have offered their own perspectives. Their accounts have varied, highlighting that life inside the Playboy Mansion was not experienced the same way by everyone.

Hefner died in 2017 at age 91, but discussion surrounding his legacy continues. Madison has since documented her experiences in her memoir, describing the contrast between the glamorous lifestyle outsiders imagined and the reality she experienced behind closed doors. As more former insiders share their stories, the once carefully curated image of the Playboy Mansion continues to be examined from very different perspectives.