Secret Admirer

Shortly after becoming Ashlyn, Jake Matthews began receiving gifts accompanied by enigmatic messages: flowers, perfume, and a pair of boots signed from "Your Secret Admirer." The notes made reference to Ashlyn's appearance, saying she had "the body of a Venus" and that she would "look sexy" in the boots. Futhermore, the first gift's note contained a PS reading "I know the real you," implying the secret admirer knew Jake's true identity.

This was confirmed beyond doubt when the admirer sent a gift certificate to Anthony, the manager of a strip club where Ashlyn had auditioned sometime before transforming. The certificate did not indicate to Anthony that the admirer was not his, but Ashlyn later learned the return address was that of the Trading Post Inn.

Ashlyn also later received a scooter, an iPod with Jake's CD collection loaded on it, and a ticket to a Red Sox-Yankees game. Jake (who by this time had official adopted the identity of Ashlyn as permanent) was advised by Jessica that this "admirer" was a stalker, and not to keep any gifts, as doing so would empower him.

It has never been revealed whether the secret admirer was the same as the "S.A." who helped bankroll Stephen Jefferies' expansion of Jakes' graphic design business.