A widow, Lilah (Penny Barber), says goodbye to her stepson Darryl (Max Fills), who is going back to college after a period of mourning. As the weeks go by, Lilah feels lonelier than ever without Darryl in the house. She becomes desperate for intimacy and connection, so her friend Justine suggests trying A.I. companionship. Lilah goes down the rabbit hole of exploring technological innovations to stimulate herself emotionally and physically, including an A.I. who takes the form of Darryl that she eventually falls for. By the time the real Darryl comes back home for a visit, she is hopelessly obsessed with this virtual fantasy - and the only way he can pull her back to reality is by offering her a real-world version of the taboo relationship she's become dependent on.

While taking a vacation at a resort, a stepmom, Jolene, along with her husband Michael (Will Pounder), watch her stepson, Danny (David Lee) fail miserably at flirting with a girl. Michael and Jolene talk among themselves about how Danny has no luck with the ladies, and it leads to Michael suggesting that Jolene fucks her own stepson! Jolene is intrigued, and it's clear that this couple has no shame. She eventually agrees, leaving Michael and instead leading Danny to the privacy of their hotel room. That's when Jolene cheekily comes onto Danny, angling to give the meek boy a major confidence boost...