The Cul de Sac Crew feels weird about Laurie and Travis dating, but Jules is determined to play it cool. Bobby and Andy make it big when Penny Can goes global. But when Bobby starts throwing around money, Grayson confronts him about years of unpaid bar tabs. Meanwhile, Andy struggles to get Stan to sleep after a slasher movie.
After letting her car insurance lapse, Jules winds up in a car accident with an attractive man named Sam. When Jules notices that her wedding ring has fallen off during the fender bender she cannot resist accepting Sam's offer to take her on a date. Meanwhile, Bobby takes steps to prepare for a major snowstorm. But with only a 10% chance of snow, the weather has Travis concerned that his dad will be disappointed.
Jules and Grayson receive a wedding invitation from a couple they barely know and on a date that conflicts with Grayson's roller-hockey finals. Despite Grayson's important plans, Jules simply cannot say no. Meanwhile, Bobby finds out that Dog Travis has puppies, and the crew discovers that Tom has created a model of the neighborhood with eerily lifelike dolls of everyone.
The town of Gulf Haven is transformed into a pirate's cove for Buccaneer Week. Determined to step up his mayoral duties, Andy pleads with Ellie to appeal to tourists by bringing out her alter ego, Charming Ellie. Enamored by this new, lovable version of her best friend, Jules cannot get enough of "Chellie." Meanwhile, Laurie starts baking "naughty cakes" to increase sales.
Andy organizes a Gulf Haven 5k in an effort to save his reputation as Mayor after an embarrassing article comes out in the local paper. Jules uses the race to help her dad Chick get out of the house and relive his coaching days. But the crew struggles to get through his intense workouts. Meanwhile, Grayson fulfills his dream of being cast in a commercial; however, he's in for a big surprise when he receives his role.
Laurie teaches Jules the rules of karma after Jules lies to customers at the annual cul-de-sac yard sale. Andy uses some of his new yard sale purchases to test Ellie after they make a bet that she can't refrain from being snarky for one day. Meanwhile, Bobby must overcome his fear of rollercoasters to fulfill his grandfather's dying wish.
With Travis graduating college in a few months, Jules starts to worry about his job prospects with an art degree. Laurie and Ellie pose as a lesbian couple in a desperate effort to get Stan into a fancy new school. Meanwhile, Andy insists on making a cat video with the guys for Bro-day.
After Travis and Laurie have Jules and Grayson over for a sophisticated brunch, Jules attempts to prove that she and Grayson are the better couple. Andy plans a beach day for Stan so he will be considered a fun dad. Meanwhile, Tom helps Ellie finish a teen novel she started writing years ago.
After Jules receives a large commission check, she enlists Andy to be her business partner in a get-rich-quick scheme. Meanwhile, Grayson tries to seem cool to Travis's new hipster friends, and Bobby struggles to feel comfortable with his new bag.
Travis starts an open mic night at Coffee Bucks, but things go awry when Andy tries to do stand-up comedy. Tom's daughter Haylee comes to visit, and Grayson and Jules decide to play along when they discover that Tom's been lying to Haylee in order to make himself sound cool.
When Bobby's boat goes missing, Jules and Bobby step into their old crime fighting personas, "Blacktop" and "Gumshoe", in order to solve the mystery. Meanwhile, Grayson helps Andy win over his new supervisor by teaching him "the neg," and Laurie and Travis attempt to decorate her apartment together.
As Chick deals with the fallout from his first Alzheimers symptoms, Jules convinces him to look at houses nearby. Without meaning to, Grayson introduces the idea of Chick moving in with them, a suggestion he quickly regrets. All the while, the Cul de Sac Crew excitedly prepares for Travis's college graduation which kicks off, among other things, a rivalry between Ellie and Laurie for who is #1 on Jules' most-important-friend list.
After winning Cul de Sac Crew Trivia, Tom gets to pick the location of the next group vacation. The gang is less than thrilled, however, when Tom opts for a stay-cation. Meanwhile, Jules fakes being healthy at her annual physical exam and gets some shocking results. And Bobby accidentally signs Grayson and himself up for a breakdancing competition.