Donna is stunned to learn that her parents have separated and initially thinks Felice's cold, difficult personality is the reason, but Noah finds out that Dr. Martin is having a mid-life crisis and still loves his wife, eventually convincing Donna's dad to return to his wife. Gina gets hit from all sides when a lucrative house-sitting job for Oksaina Baiul ends with her painful firing, Kelly says she loves Dylan while being hypnotized, and she's nearly raped only to have everyone think she's lying about it. Gina and Dylan ultimately reconcile but Kelly and Dylan remain in each other's thoughts. Elsewhere, David finds out the DJ he worshipped has become a shunned dinosaur and contrives to get his hero a second chance, and Steve and Janet do a story on a child prodigy that brings up out some regrets for Janet over her past.

Kelly and Matt babysit Erin, and have sex in the living room after she goes to sleep. They do not realize that Mel and Jackie have set up a video camera to observe prospective nannies with Erin. Erin switches the tape with a copy of "There's Something About Mary," and the illicit video ends up in Dylan and Gina's hands. Dylan becomes furious, prompting Gina to suspect that he still has feelings for Kelly. She believes that Dylan is trying to overcompensate by arranging a private concert by Monica, and tricks him into admitting that he slept with Kelly in Mexico. Matt breaks up with Kelly, who reminds him that he was married at the time. He forgives her after she insists that she never revealed the truth because she did not want to add to his woes. Donna asks Wayne, a good-looking pro beach volleyball player, to model her new line of men's wear. Matt files a lawsuit on behalf of cancer victims against a number of companies that polluted the environment—including Hunter Oil. Noah refuses to cooperate, and suggests that he and Donna live together so that he can move away from Matt. Donna hesitates because of her attraction to Wayne, whom she kisses in a restaurant. Steve panics about the possibility of massive computer failure on New Year's 2000, and becomes obsessed with stockpiling supplies. Janet believes that he is just trying to avoid the romantic vacation they had planned for New Year's. Steve explains that he is gun-shy about relationships because Celeste, Carly and Clare all dumped him; Janet promises not to leave. Katie sleeps with David, then has difficulty dealing with it and says she must abstain for at least a year. David admits that he cannot handle this, and breaks up with her.