Simon is a member of the Castlebury police department and works for Maggie Landers' father. Simon is Maggie's secret lover while she is dating her boyfriend Walt. Maggie and Simon sleep together in his police car regularly.
Maggie ended their relationship when Donna saw them together and threatened to tell Walt. Later Maggie learnt that Simon had a girlfriend. In the last episode of Season 1 after Maggie kissed Sebastian (Carrie's Boyfriend). Maggie then gets pregnant with Simon's baby, though she doesn't end up having the baby, and almost died, Maggie still tells her dad that Simon was the one who got her pregnant (not Sebastian) which leads to Simon getting fired and divorced. He comes to their school looking for Maggie and gets in a fight with Sebastian which causes Sebastian to get expelled.