Jules, not wanting to spend Valentine's Day alone, turns to Grayson to keep her company when everyone else makes plans. Meanwhile, Bobby and Jules take different sides when Travis asks to go to a party where they know he will be drinking; Ellie tries to prove she is the alpha dog, not Grayson; and Laurie meets Smith's father.

Jules has mixed feelings when Travis gets accepted to two of his choice colleges. Now he must decide between schools in California or one just 20 minutes from home. As Jules struggles with the thought of Travis moving away, Grayson is there for her. Meanwhile, Laurie considers her feelings for Smith when he returns from law school, and Andy longs for the freedom to do whatever he wants around the house, free of Ellie's rules.

Jules schemes to continue giving Bobby money when he stops taking alimony payments. Ellie ticks off the gang by being arrogant about her intelligence.

Jules wants to help Bobby gain his confidence back and thinks fixing up his boat and getting it back in the water will do the trick.

As Travis continues on a downward spiral from his breakup with Kirsten, Jules decides it's time to give him some tough love.

Jules has a hard time accepting that Holly is part of her life, a situation that does not improve after she finds out that Holly and Travis made out; Andy wants to run for mayor so he can change the town rules against weddings on the beach (something Jules has her heart set on), but Ellie won't let him; and Laurie tries to convince Bobby he's just socially inept, not prejudiced, after he blurts out some awkward comments at the cake shop.

Jules plans a spring Thanksgiving after realizing the gang didn't celebrate the holiday together; Ellie's parenting skills are called into question when Stan gets a hold of Big Carl; Grayson helps Andy prepare for an annual pizza toss.

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.