Corky gets lost and wanders around the mean streets of Chicago. He meets a kindhearted, young hooker who gives him his first sexual experience-essentially a few long kisses. ( The episode is intentionally vague over whether they went further.) Corky is shadowed (and mystically guided) throughout the evening by a semi-mythic blues singer, the great Leon Redbone. Becca and Tyler spend a rainy, frustrated evening driving around Chicago looking for Corky, and end up smooching in the car. This episode was filmed mostly in black and white.
Cupid is shooting arrows at almost everyone. First Hans gets a crush on a lady that delivers newspapers whose husband just died. Kent, Paige's motorcycle man returns and aings ""Wild Thing"" to her at the Grill and they get back together. Becca has to dissect a frog in biology and her partner is a boy named Matt. They have an up and down relationship but still end up together rather than as friends. Tyler catches them smooching in the hall and becomes jealous. He sneaks into Becca's room that night and proclaims his feelings to her only to find out that it is Zoe he is talking to...Becca is out with Matt. Jerry develops a crush on Gina and they go out on a date provided that only the human part of Jerry is allowed on the date and if Jerry shows up, the date is over.
Corky resolves to enter a 50k bike race despite his father's objections, and makes friends with another biker who is epileptic. He bought a brand-spanking new bike from a guy in the bike store who had a crush on Paige. The bike was stolen, and Zoe, seeing Corky's heartbreak, stole him an almost identical one. The truth wins out, though, and all gets cleared up in the end.
Becca gets a crush on a French student and Maxi with this French guy's friend. They have high hope of getting in with this ""mature"" crowd. She and Maxi go to a bar with these boys and Maxi gets drunk. Becca tells her mom the next morning to get some help for Maxi's hangover. Becca's mom ends up telling Maxi's mother what happened after giving her word to Becca that it was just between them. Becca and Maxi get into a fight and Maxi is in with the mature crowd. Becca ditches school and gets grounded but has to go out that night when she recieves a call from Maxi because one of these guys had left her stranded. She gets caught sneaking back in the house. Side plot: A lady is choking in the restaurant, Corky runs to get Drew who gives the lady the Heimlich maneuver and the two of them become heros. Later the lady sues Drew for $ 25,000 because supposedly he broke one of her ribs.
Becca dreams about figure skating with a man. She wakes up with the chicken pox and has to stay home sick. Tyler comes to visit her several times to tell her about his problems with Rona. He and Becca become closer until Rona shows up ( just when they're about to kiss!)and steals him back from her. Meanwhile, Drew hires a waitress at the grill and comes down with the pox. Corky also gets sick and thinks that Becca got him sick on purpose. Paige's boyfrind (the vet) has gone to a conference and then will be moving back home to take over his father's practice. She wants Libby to go to a spa with her that weekend and think about going with him. The decision is made for her when she finds out the vet wants to get married to a another woman. After all 3 Thatcher's get over the pox, Libby comes down with a nervous rash from all her stress and is bed-ridden for the weekend and left to fend for herself.
Drew decides to turn the back room of the restaurant into a banquet room in hopes of bringing in more money. He gets funding from Farmer Jack on the condition that Drew use his son (Teddy) as a worker. Drew agrees. Drew and the kid develop a father/son like relationship. Corky is jealous and tries to help but causes more damage than good, which Drew blames on Teddy until Corky tells him the truth. Meanwhile, Libby, back at her old job tries to dig up a canine star for a gourmet dog-food commercial.
Rona and Tyler break up because Rona lied to him and went to a frat party. Becca becomes manager of Tyler's band and sets up a gig for them at the opening of the new mall with the prerequisite that there has to be a female singer in the band. Tyler asks Becca nad she agrees. At the last minute she backs out and asks a friend to do it and Tyler ends up leaving with Becca's friend, leaving the Bec depressed. Also, Libby is offered a chance to leave the restaurant and return to her old high-pressure, but higher-paying job.