Annie discovers that the particularly flirtatious mother of one of Lucy's friends, Serena is seeing Eric for therapy sessions. Annie strongly requests that he refers her to someone else. Annie then has to deal with the guilt over her jealousy-induced interference between the two. Also, Simon is mortified when word gets around school over the fact that he's a virgin. Annie had shared the details of Simon's sexual inexperience with his ex-girlfriend's (Sasha) mother, Rita. Meanwhile, Matt struggles about telling Robbie he's interested with his ex-girlfriend, Cheryl. Lastly, Robbie is also hiding a secret from Matt that involves his ex-girlfriend Heather.

A startling breakthrough leads to a renewed connection for two of the gang. Differing reactions to a life shattering event creates tension among the gang, resulting in heartfelt revelations, hidden insecurities and thoughts of leaving Roswell. Meanwhile, Liz enlists Sean in her continuing quest for answers into the death of Alex.

After meeting another AI, Rommie has to deal with an artificial version of love. Soon after the meet the question becomes what motives does Rommies new love interest have for her.

John takes an out-of-shape patient (Alan Blumenfeld) to a gym to work out, but the man has a heart attack there and then sues John; Linda dyes her hair blonde and suspects that's the reason people think she's dumb.

Larry defends Sting when a man sues him for breaking up his marriage; a Streisand impersonator sues over his nose job; Richard flirts with Cindy Margolis to make Ling jealous.

Sean, Jason and Zack are headed to the Big Island to participate in the Showdown 2001, a 12 mile course of natural obstacles. Leigh will be taking over supervisory duties while Sean is away. J.D. is tending to Kekoa, who has come down with the flu. Fortunately, J.D. has an iron constitution, despite the fact that he didn't have his annual flu shot. Jason has always wanted to participate in the Showdown 2001, and this looks to be his big chance. However, as part of their sponsorship by Trail Tracker magazine, they need to take along a reporter who will participate. It turns out to be none other than Jessie. This is her big chance to change her career and make something of herself. Sean reminds her that the team will still be playing by all the rules, and there will be no exceptions made to help sell her story. Jessie is agreeable to these terms. She, though, has already chosen who her partner will be: Jason. He is not happy with this, since he still holds a grudge based on the way she b

Doug, Carrie and Arthur head out to the airport to visit with Doug's parents while they have a short layover at Kennedy Airport on their way to Montreal. While there, his parents ask him to sign their living will, making him the one responsible for pulling the plug. When his sister Stephanie gets wind of this, she is offended that she wasn't the one asked to be responsible.

Tonight, actor Eric McCormack from Will & Grace.

Victoria Merrick has a tough time when a teenager steals her wallet, and Janice Taylor gives her a dressing down.