Stuart turns up in Erinsborough and his friend, Drew Kirk allows him to stay with him and his wife Libby Kennedy (Kym Valentine). Stuart secures a job at Carpenter Mechanics. Stuart begins a relationship with Dee Bliss (Madeleine West) and she invites him to move into Number 30. Stuart's ex-fiancée, Tracey Slattery (Christine Wools) shows up in Ramsay Street and Stuart explains that she cheated on him on the eve of their wedding. Upon Tracey's departure, Stuart and Dee break up. Stuart then develops feelings for Felicity Scully (Holly Valance). Stuart joins the army, but he is not happy and decides to take a job as a hospital porter instead. Following Drew's death, Stuart promises Libby that he will be there for her and he quits his job at the hospital. Shortly after becoming a couple, Felicity tells Stuart that she is leaving for New York. Stuart proposes to her and she accepts. Once Felicity leaves, Stuart begins spending time with Libby and her son, Ben Kirk (Noah Sutherland). Stuart later admits that he made a mistake getting engaged and calls Felicity to tell her that their relationship is over. Stuart finds the garage hard to run by himself, and he employs Stephanie Scully (Carla Bonner). Stuart is accused of causing Dee's death when the car Toadie was driving on their wedding day is not deemed roadworthy.