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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.
Simon became close to Tiffany's boyfriend Tony Hills, who had earlier been secretly confused about his sexuality, but decided not to act on his feelings after he fell in love with Tiffany. However, while on a trip to Blackpool, Tony was unable to control his urges any longer and kissed Simon. Simon wrestled over whether to tell his sister what had happened, but when Tony claimed it meant nothing, he kept quiet, although he spent a lot of time trying to convince Tony to confront his demons.
Simon eventually got to the point where he had had enough of Tony's denials and unpleasantness and so he decided to move out of the flat. That night, after having packed his bags earlier in the day, Simon told Tony of his intention to move out of the flat and in response Tony begged him to stay. Simon demanded to be given a very good reason why he should do so. Then followed a torturous discussion during which Tony eventually admitted his homosexuality and his love for Simon, after which they cuddled and kissed.
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.
Simon and Tony stayed together for a while, and Simon even reconciled with his father and mother, who both appeared in Walford in search of their children. Simon initially worked on Sanjay Kapoor's market stall selling clothes, then later for his sister's best friend Bianca Jackson. Simon's idyll was shattered, however, when he found out that Tony slept with the female singer Frankie Pierre, as well as his work colleague, the reporter Polly Becker. Angry and devastated, Simon ended the relationship.
An old friend from Manchester, Jonathan, got in touch when he was helping another friend, Chris, move down to London. Although Simon initially thought they were a couple, it became clear that Chris was taking a shine to Simon, with some not so subtle flirting. After breaking up with Tony, Simon immediately started seeing Chris, even though Chris wanted and 'open' relationship with freedom to see other people. Initially this seemed to be a relationship which may work, but based on previous experiences Simon started to read more into Chris' clubbing and friendships with old boyfriends and he started to become jealous. It was while he and Chris were on holiday with Tony,Teresa di Marco, Mary Flaherty and Matthew Rose, that Simon and Tony realised that they still had feelings for each other. The main reason for the holiday was for Simon and Chris to sort out their relationship. They did: Simon ended it as he didn't love Chris.
When Tiffany was killed in a car accident on New Years Eve 1998, Simon had a nervous breakdown and blamed Tiffany's husband Grant for her death. This culminated in Simon abducting his sister's baby, Courtney, and taking her to Peacehaven, where he stood by the edge of a cliff and threatened to jump with Courtney. After much abusive ranting, Grant and Tony persuaded Simon to hand Courtney back and Simon was taken home to recover. His mental health only deteriorated, however, when he discovered that his mother had been sleeping with Grant behind his sister's back (which famously led up to the events of her death that same year). Distraught, Simon accidentally set fire to his mother's flat while he was trapped inside. Simon was badly burned and was taken to hospital to recover.
Upon his return, Tony had decided that Simon was the man for him and Simon accepted the fact that Tony was not gay but bisexual. When Tony left Walford to travel around Europe, Simon went with him. His last appearance was in 1999.