Kurt, Brian and Susan celebrate Simon's birthday by breaking into the school. After facing the wrath of Jenny, Simon seeks relationship advice from Susan.

Simon suffers under Jenny as Acting Head of Year when Arnie is found with cannabis; this results in a drugs talk and Simon upsetting new girlfriend, Maggie. Susan prepares to apply for the role of Head of Year herself.

Simon's personal life suffers when his dad invites his girlfriend, and her daughter, to move in with them; he seeks further advice from Susan regarding Maggie as she is still upset with him.

Simon helps Pauline and Cheryl sort out problems with their love lives; this goes disastrously wrong when he mentions the problems to Kurt and Brian. Simon is concerned that his relationship has hit a low point sexually.

Sharing Kurt and Brian's flat is too much for Simon, so after list writing he moves in with Maggie. Between this and the flat warming party, Simon and Jenny's friendship becomes less icy.

While Simon faces the truth about his father, the school is littered with pornographic images. Simon finds himself between a rock (Pauline's chest) and a hard place (Bob's office) which is something he cannot get someone else to do.

Simon is haunted by nightmares as his job interview approaches. While Kurt and Brian want Simon to get the job, they are distracted by a female applicant. At the Xmas party Jenny does something she might come to regret.