Sydney 'Syd' Woolfe first appeared in Emmerdale in March 2002, as a builder working alongside Jerry 'Mack' Mackinley. Upon his arrival, Syd caught the eyes of many female residents due to his good looks and his charming nature. Syd moved in with local mechanic Scott Windsor and his girlfriend Chloe Atkinson. After Mack left the village Syd remained there to continue work. He became best friends with Scott, but found himself attracted to Chloe. However, initially he didn't let his heart rule his head and decided to keep his feelings to himself, in the meantime enjoying flings with Angie Reynolds and Nicola Blackstock.