According to Thought Catalog, every day of the week for Hefner’s girlfriends was planned. Some days they went clubbing with Hefner, other times they had to be present for his parties and weekly movie nights. On the days that didn’t have any scheduled activities, the girls were expected to be back at the mansion by 9 p.m. Although they were given a weekly $1,000 allowance for clothing, saving it was frowned upon. Per Showbiz Cheatsheet, Hefner’s girlfriends were expected to join him for a biweekly orgy that they dreaded. He was also said to encourage jealousy and competition between the girls (via E! Online).
In a 2021 interview, Madison (above), Hefner’s girlfriend from 2001 to 2008, said that being in a relationship with him felt like “Stockholm Syndrome” (per Best Life). Us Weekly reports that although Madison felt like she was in love with Hefner, he often lashed out at her. Despite this, she felt guilty for even thinking about leaving. Madison went on to suffer from depression and suicidal thoughts while living at the mansion. She only left when Hefner refused to wed and their attempt to have children failed. Madison has gone on to say that living in the mansion with Hefner and his other girlfriends was cult-like and cutthroat (via 9Honey).