Corky wins a church raffle prize of an all-expenses-paid trip to Hawaii for the family. But his plans to give Libby and Drew a second honeymoon soon become plagued with many problems.
After a few snafus, everything is going swimmingly for the Thatchers on their Hawaiian vacation with Corky riding with the dolphins and Becca falling for a surfer.
Becca becomes manager of Tyler's band and sets up a gig at the opening of a new mall with a prerequisite of a female singer. Also, Libby is offered a chance to leave the restaurant and return to her old high-pressure, but higher-paying job.
Drew gets funding from Farmer Jack for a new banquet room for the restaurant on the condition that Drew use his son Teddy as a worker. However, this results in jealousy from Corky who tries to help but causes more damage than good.
Libby is forced to take care of everything when Becca, Drew, and Corky all come down with chicken pox. During her illness, Becca draws even closer to Tyler who has broken up with Rona again.
Becca and Maxie have high hopes of getting in with the "mature" crowd which brings their friendship to a low. Elsewhere, Corky and Drew become heroes to a choking woman; only to get Drew slapped with a $25,000 lawsuit.
Tension between Becca and Drew isn't helped by the arrival of Libby's sister Gina and niece Zoe. Unfortunately, an even greater strife between the sisters lands Libby in the hospital.
Corky resolves to enter a 50k bike race despite his father's objections, and makes friends with another biker who is epileptic. Sadly, his happiness turns to heartbreak when his brand-new bicycle gets stolen.
Cupid is shooting arrows at almost everyone: Hans gets a crush on a widowed lady; Paige's motorcycle man revving back to her; Becca hopping for her lab partner; and Jerry developing a crush on Gina.
Becca organizes a '60s-style protest in support of a record store owner arrested for selling allegedly obscene material. She begins having nightmares of "Thought Police" (censorship cops) storming through Glen Brook.
Corky gets lost and wanders around the mean streets of Chicago leaving Becca and a newly single Tyler to spend a rainy, frustrated evening driving around Chicago looking for him.
Drew confronts his feelings about him and Libby having another child. Meanwhile, Becca makes a muck over an athlete's unearned grades--only to muddy herself.