Jenny challenges Ross to start acting like the boyfriend she secretly wants him to be. Cliff helps Evan nab the guy he wants. Sarah, tired of competing with his computer, gives her boyfriend Jake what every guy hates most...an ultimatum.

Ross rises up to Jenny's challenge to act like her boyfriend--and then she decides to move back to Ohio just as he thinks he might get to like the situation. Jake suspects that the radiation from his computer had begun to sap his sexual prowess. College sex-advice maven Emma can get everyone to open up except her monosyllabic boyfriend Brian.

Jenny suddenly returns to Ross' pad after a last minute decision not to move back to Ohio, but Ross has had a chance to think over the long-term commitment. Sarah tries to get her paranoid boyfriend Jake to pay attention to her by hitting on his sleazy buddy, Steve. Emma encourages her college boyfriend Brian to let go of his inhibitions by communicating through a sock puppet he names "Mr. Fuzzy."

An enigmatic message on Sally's answering machine makes her think her beau Stan wants to break up, so she vows to find out what's wrong with her by interviewing all of her ex-boyfriends. Jake realized his fear of commitment to Sarah comes from his family's past, but Sarah suddenly develops her own commitment fears. Emma's transference therapy with Brian backfires when he can't be intimate with her without "Mr. Fuzzy."

A "Fearsome Foursome" of high school girls with wicked gossip and backstabbing on their minds makes a bet that whomever brings down one of their rivals will get to have the hot new single guy. Sally arranges to speak to all of her exes to discover why her current guy, Stan, might be thinking of breaking up with her, and the first on the list is the sexual stamina king, Jake. Emma and Brian discover that their last bout of sex-with-sock-puppets accidentally went out over the internet via her Web site.

To win a competition to bring down popular rival Jeanine, Liz steals her diary, which contains some pretty nasty revelations that threaten the Fearsome Foursome. Sally interviews Bill, a boy who suddenly dumped her for a trip to Fiji, and finds out that he still loves her. When Brian can’t have sex with Emma without his sock puppet, she decides to hide "Mr. Fuzzy."

The Fearsome Foursome find more nasty revelations about themselves in the diary stolen from their archenemy--but who is the snitch who sold their secrets? Still trying to discover why her boyfriend Stan may want to break up with her, Sally springs an interrogation on the delivery guy and almost drives him to a breakdown. Emma finally adapts to Brian’s use of a sock puppet for sexual communication with her, but she won’t tolerate him using it with anyone else, especially the free-thinking Kiki.

Stacey and Debbie trap their intended date for the dance, Jonas, in a revealing game of Truth or Dare, and Liz tries to rope her sister's boyfriend Kyle into the game. Stan unexpectedly comes back from San Francisco a day early, and finds his girlfriend Sally interviewing her boyfriend from elementary school, Chuckie. Dean has a co-ed bathroom romance going with Claire, but he's frightened of their growing intimacy because he's still a virgin.

Doc and Rory prowl the seedy underworld of suburbia in Rory's van, but tension still simmers between them because Rory stole Doc's ex-girlfriend, Jana. Dean tries to romance Claire but blows it, so Emma advises that he soothe his fears of virginity by sleeping with the dorm's easy girl, Kiki. When Tina gets her older sister Liz grounded, Liz gets back at her by hinting that she's done something ballsy to Tina's boyfriend.

Tina gets her older sister Liz grounded, Liz gets back at her by hinting that she went down on Tina's boyfriend Kyle, and Tina tries to increase the heat with Kyle to keep him focused on her.

Rory takes Jana to an isolated park in his van, and discovers the complex engineering involved in removing a girl's bra. Claire learns that Dean wasn't a virgin the night she slept with him--Kiki had hopped in the sack him only a half hour before--and she's furious. Tina asks her boyfriend's best buddy Jared to teach her the art of the hummer so she can win back her boyfriend.

After losing his virginity to the wrong girl, Dean is given another chance with Claire on one condition: to agree to a period of celibacy as part of a re-virgination process. Kyle wants to know where Tina picked up her new oral pleasure skills, and is shocked when she tells him it was his best friend Jared that taught her. Andy stumbles across his lover Joel's porn stash...straight porn...and worries that Joel may secretly be bi-sexual.