In the Season 5 finale, Tom wins Cul-de-Sac Crew Trivia, so he gets to pick the destination of the next group vacation, but they're disappointed by his idea for a staycation. Meanwhile, Jules' annual physical yields some surprising results after she fakes being healthy; and Bobby inadvertently signs Grayson and himself up for a break-dancing contest.
Chick's Alzheimer's symptoms prompt Jules to urge him to look for a house in her neighborhood, but Grayson's inadvertent suggestion that Chick move in with them is one he regrets. Meanwhile, the cul-de-sac crew prepare for Travis' college graduation, which reignites the rivalry between Ellie and Laurie for the top spot on Jules' list of friends.
Bobby's boat disappears, so he and Jules assume their crimefighting alter egos, Blacktop and Gumshoe, to find it. Meanwhile, Grayson gives Andy advice on how to win over his new supervisor; and Laurie and Travis try to decorate her apartment.
Travis starts an open mike at Coffee Bucks, but probably wishes it were closed when Andy starts doing stand-up comedy. Meanwhile, Tom gets a visit from his daugher, who's under the impression that her dad is much cooler than he actually is.
Grayson tries to act cool in front of Travis' hipster friends. Meanwhile, Bobby gets a new bag, but doesn't feel comfortable carrying it; and Jules hatches a get-rich-quick scheme with Andy after receiving a big commission check. Directed by series star Josh Hopkins.
Brunch at Travis and Laurie's prompts Jules to prove that she and Grayson are the ideal couple. Meanwhile, Andy tries to be a fun dad by taking Stan to the beach; and Tom helps Ellie finish a teen novel she hasn't worked on in years. Directed by series star Courteney Cox.
Travis is ready to graduate from college, but Jules worries about his job prospects with a degree in art; Ellie and Laurie pretend to be a couple to get Stan into an elite school; Andy is determined to make a cat video for Bro-day.
The annual cul-de-sac yard sale gives Andy a chance to bet Ellie she can't stop being snarky for one day, while Laurie schools Jules on karma after the latter lies to a customer. Also: Bobby tries to overcome his fear of roller coasters to fulfill his grandfather's final wish.
Andy organizes a 5km race to salvage his reputation as mayor after an embarrassing article runs in the local paper. Meanwhile, Jules asks her dad to get the cul-de-sac crew in shape for the event to relive his coaching days; and Grayson fulfills his dream of being in a commercial, but his role isn't what he'd imagined.
Buccaneer Week in Gulf Haven turns the town into a pirate's cove, and Andy hopes to bring in tourists by convincing Ellie to trot out her charming alter ego, much to the delight of Jules. Meanwhile, Laurie tries baking risqué cakes to boost business.
Jules and Grayson get a wedding invitation from a couple they barely know, but the event falls on the same day as Grayson's roller-hockey championship. Meanwhile, Bobby finds out his dog has puppies; and the cul-de-sac crew learn that Tom has a model of their neighborhood complete with lifelike dolls. Directed by series star Courteney Cox.
Jules gets into a car accident with a handsome stranger (Matthew Perry) who winds up asking her out since her wedding ring fell off during the incident. Meanwhile, Bobby prepares for a major snowstorm even though the chances are extremely remote. Directed by series star Brian Van Holt.
The fifth season begins with Bobby and Andy hitting the big time when Penny Can becomes a global sensation, but Bobby's newfound wealth is the perfect time for Grayson to remind him of all his unpaid bar tabs. Meanwhile, Laurie and Travis' relationship takes some time for the cul-de-sac crew to get used to; and Andy has trouble getting Stan to sleep after a horror flick.