Simon is the older brother of Tiffany Mitchell. Their mother, Louise left the family home when Simon and Tiffamy were young leaving them to be brought up by their abusive and alcoholic father Terry. Simon who had come to terms with his sexuality got involved in a relationship with another man called Howard. This came to an end when the relationship became abusive and Simon left for Walford to search for Tiffany.
Simon arrived in Walford in June 1996 looking for his sister Tiffany Mitchell. He soon settled in Walford and fell for local boy Tony Hills, who happened to be Tiffany's boyfriend. Following a kiss in Blackpool Tony, who was still confused about his sexuality, claimed it was a one off and he still loved Tiffany and Simon decided to keep quiet. Following a tortuous couple of months where Simon tries to encourage Tony to accept his sexuality Simon cannot take it any longer and offers him an ultimatum either Tony gives him a reason to stay or he will leave Walford for good. Tony admits his true feelings for Simon and kisses him passionately when they are interrupted by Tiffany.
Simon and Tony have an on off relationship during the rest of their time in Walford before leaving to travel the world together.