Kendra reveals that Hefner had once encouraged her to take Holly’s usual place beside him during mealtime. When Kendra demurred, warning that this would cause drama, Hefner stomped “his feet and was like, I like the drama” (241).

Producers of the final episodes of season five want to add a montage of romantic moments between Holly and Hefner. They badger Holly to record a voiceover for it, which she refuses to do. The producers criticize her refusal to sugarcoat the breakup with Hefner.

Despite the fact that they have officially said goodbye, Hefner continues trying to sabotage Holly by criticizing her in the media and comparing her negatively to other women in his life. Holly responds by angrily ordering him to stop.

Holly’s relationship with Criss turns romantic. She moves into Criss’s Vegas hotel suite and attends all of his performances. Holly is among the few bright spots in his life, as critics are panning his new television program.

Initially their relationship is a perpetual honeymoon, filled with expensive gifts, exotic trips, and romance.  But like Hefner before him, Criss slowly restricts her freedom. Not only does he demand access to her phone, but he also begins making rules about where Holly can go and with whom she spend time.