Naomi finds herself in trouble when she fails an assignment, and Ryan and Kelly bring the issue to Harry's attention, while Harry struggles with a disturbing revelation about the result of a secret tryst with Naomi's mother, Tracy, from many years ago. Meanwhile, Dixon learns more about Navid when they team up to try to pull a school prank against Palisades High. Annie meets a potential love interest in the form of drama student Ty Collins, who turns out to be the wealthiest student at West Beverly, and who spirits her away for San Francisco for the evening. Silver posts the story about Ethan's infidelity with Naomi on her Internet blog, while Adrianna continues her self-destructive slide into drugs and debauchery. Also, Ryan tries to ask Kelly out on a date, but she has to find a babysitter first for her four-year-old son, and former West Beverly alumni Brenda Walsh, now a successful Broadway and London theater director, arrives back in town to help put on a new school play.