Jules finds it difficult to cope with Travis and Laurie being a couple, now that the relationship has become very physical. Meanwhile, "Penny Can" has gone international and Bobby starts receiving royalty checks. Bobby then goes on a frivolous spending spree, causing Grayson to not-so-politely remind him of his years-overdue bar tab.

Jules forgets to pay the bills after moving them online, which results in her car insurance lapsing. Her wedding ring slips off her finger while driving, and in trying to retrieve it she crashes into a wealthy man named Sam (guest star Matthew Perry). In exchange for Sam overlooking the accident, Jules agrees to date him. Meanwhile, Bobby prepares for a big snow after hearing there's a slim chance of a few flakes falling in Gulfhaven, and Ellie tries to poke holes in Laurie's long list of amazing life stories.

Jules' people-pleasing ways gets her in trouble when she can't say "no" to a clingy couple that bought a house from her. Bobby discovers that Dog Travis has pups, and he asks Ellie to help him fight a joint custody battle. Meanwhile, Tom has built a scale model of the cul-de-sac in his garage, complete with remarkably detailed figurines, and Travis makes a comment about the Laurie figure that upsets her.

The town is transformed into a pirate's cove for Buccaneer Week. Andy pleads with Ellie to appeal to tourists by bringing out her alter ego, "Charming Ellie", attempting to step up his mayoral duties. Andy's friendship with Bobby is tested when Bobby tells a crowd of tourists that the beach needs to be closed after he spots a large jellyfish. Meanwhile, Laurie starts baking "naughty cakes" to increase sales.

Andy organizes a 5K run in an effort to save his reputation as Mayor after an embarrassing article comes out in the local paper. Jules uses the race to get her dad out of the house and relive his coaching days, but the crew struggles to get through Chick's intense workouts. Meanwhile, Grayson attempts to get back into acting and is excited about landing a role in a commercial, until he realizes it's for an erectile dysfunction product.

After Jules lies to customers at the annual cul-de-sac yard sale, Laurie teaches her about karma. Andy uses some of his new yard sale purchases to test Ellie after betting her that she is unable to go a whole day without being snarky. Meanwhile, Bobby must overcome his phobia of rollercoasters to fulfill his grandfather's dying wish.

With Travis graduating art school in a few months, Jules starts to worry about his job prospects. Laurie and Ellie pose as a couple in a desperate attempt 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 brunch, Jules attempts to prove that she and Grayson are the better couple. Andy plans a beach day for Stan to try and convince him that he is a fun dad. Meanwhile, Tom discovers a draft of a teen novel (Travellers) in a box of yard sale junk he purchased, and he tries to help Ellie finish it after she reveals she started writing it years ago.

Jules enlists Andy to be her business partner in a get-rich-quick scheme after she receives a large commission check. Meanwhile, Grayson tries to act cool around Travis's new hipster friends, and Bobby struggles to feel comfortable with his new man-bag.

Travis starts an open mic night at Coffee Bucks to bring some culture to the venue, but his plan backfires when Andy shows up with his lame stand-up comedy act. Meanwhile, Tom's daughter Haylee (guest star Julianna Guill) comes to visit, and Grayson and Jules hesitantly play along when they discover that Tom's been lying to Haylee, saying Jules is his girlfriend.

When Bobby’s boat suddenly goes missing, Jules and Bobby bring back their detective personas, "Blacktop" and "Gumshoe", in order to solve the mystery. Grayson helps Andy win over his new supervisor by teaching him "the neg," and Andy later tries the technique on Ellie. Elsewhere, Laurie and Travis attempt to decorate her apartment together as couple, which leads to their first fight.

Chick decides to move closer to Jules after his Alzheimers begins to worsen, while Travis prepares for his graduation ceremony. Meanwhile, Ellie and Laurie rivalize over which of them is Jules' #1 best-friend.

Jules cheats on her physical exam, then gets unexpected news when the urine sample she got from Laurie shows that Laurie is pregnant. Laurie and Travis face a possible break-up after Andy puts them in a fake marriage to help him at his job, and they realize they want different things in life. Now it's up to Jules to fix things and reveal the news to them. Meanwhile, Grayson and Bobby challenge a group of youngsters to a break dancing "break-off", but reconsider when they find out they will be grandfathers.