Weston became embroiled in a debate about ageism in Hollywood after it was discovered that she lied about her age to get work in the entertainment industry.

— Bernard Weinraub, Cosmopolitan January 1999[4]Beginning in 1987, Weston carved out a career as a film and television actor, working steadily throughout her twenties in a series of mostly small bit parts.

In May 1997, and by now using the name Riley Weston, she began claiming her date of birth as 1979 in order to be considered for further acting roles.

[10] After Entertainment Tonight began working on a segment about Weston, her real identity and age emerged[12][13] This occurred after Daily Variety published an October 15, 1998 article reporting that it had obtained court documents showing that Weston had changed her name in 1997 from Kimberlee Elizabeth Kramer, and had been born in 1966 rather than 1979.

The day the report was published, Weston admitted that she lied to nearly every individual and entity she interacted with professionally, including her agents, attorneys, colleagues, Disney, and the media.

Only her family and manager/ex-husband knew her true identity, a ruse she was able to maintain for as long as she did because, as she explained, "I don't have a lot of friends."

She also created false identification documents, wore baggy clothes typically worn by teenagers at the time, brought her mother to meetings, and made comments more common to teens, such as working as a babysitter and having a crush on popular teen idol Jonathan Taylor Thomas.

"[14]She also stated that she changed her name partially for "security reasons" due to harassment by a stalker she had faced beginning in 1993.

"[10] Weston settled in Tennessee, where she writes and performs country songs, often at the Nashville's Bluebird Café.

[16] She wrote the television film Apples, Orchards & Romance, which would air in September 2023 on Great American Family.