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 tries to help Pauline and Cheryl sort out problems with their love lives; this all goes disastrously wrong when he mentions the problems to Kurt and Brian.

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

Susan is under great pressure with the organisation of an open evening when she makes a massive decision about her marriage; she is then deeply upset that Simon lets her down and does not support her.