Simon arrived in Walford in 1996 when he came in search of his sister Tiffany, after his abusive relationship with his partner, Howard, collapsed. Their father Terry was an abusive alcoholic, while their mother Louise had abandoned them when they were young. Tiffany (who was pregnant at the time) came home, discovered them in the act of kissing, and fled the house hysterically with Tony and Simon running after her. Tiffany found it difficult to forgive her brother but they eventually reconciled when Tiffany settled down with Grant Mitchell.