Sylvia made her first appearance in Shoes, Hats, Pickle Jar Lids as Teddy’s daughter Courtney. Charlie immediately falls for her stunning beauty, but Teddy immediately asks Charlie to stay away from her. Though Charlie tries to remain faithful to Teddy, he ends up having sex with her, as she tricks him into doing so, so that she can blackmail him into buying a Ferrari. At all stages, Alan tries to stop Charlie from getting close to her, warning that she's a sociopath, but he doesn’t listen.