Jules tries to party hard like a twentysomething and ends up looking like a total fool, when even her best friend Ellie, told her not to do it. Travis discovers trying to avoid further embarrassment due to his father, Bobby, working at his school, can actually add to it. Jules gets as frustrated as she faces the physical limitations of her age.

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.

Jules rues the day when her ex-husband, Bobby, and Grayson become fast friends over a mercy golf lesson that she organized to help boost Bobby's self esteem. Meanwhile, Laurie surprises even herself when she takes on a new client to prove her worth to Jules.

Laurie needs a co-signer to buy her first condo and finds her less than stellar, absentee mother no help at all. Meanwhile, Bobby is mugged by a woman and Travis comes to Barb's aid after her latest cosmetic surgery procedure.

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.

Pilot - We meet Jules, a woman who at her twenties took on marriage and a baby instead of experiencing the dating scene. Now on her forties, she finds herself as a divorcee and eager to live the dating scene that she missed. With the help of her friend, Laurie, her younger co-worker who wants to show Jules to go out there and have fun. Ellie, her sarcastic, married and content to her average but lovable husband Andy. There's also her family, her ex-husband Bobby and her son Travis, who will test her patience, and her new forty-something divorced neighbour Gray, who doesn't believe that Jules can date again.

Jules family and friends crash the 10th date with her new boyfriend, Josh. Ellie and Laurie help Jules realize that it's ok to be selfish once in a while, when Jules has a disastrous experience in bed with Josh. Meanwhile, Jules left Travis with Bobby, who has to be responsible and deal with his son.

When Josh tells Jules he's in love with her, she knows the time has come to break things off with him. Unfortunately for Jules, she's not the best at ending relationships without hurting people's feelings, but thankfully she has the expertise of friends Laurie and Ellie to see her through. Meanwhile, Bobby, Grayson and Andy hit the links with money and pride on the line.

Scott Foley guest stars as Jeff, a very wealthy potential home buyer who is interested in one of Jules overpriced homes. Meanwhile, Ellie with reserves leaves the baby with Andy for a day to prove that she trusts in him.

A hot tennis instructor gets between Ellie and Jules, while Laurie turns to Travis for advice, and Andy and Grayson try to cheer up Bobby after a fresh heartbreak over Jules.

Sara is a confident wine rep who sets her sights on Grayson; but is he strong enough to be her man? Meanwhile, when Ellie tells Jules she can't change past a certain age, Jules is determined to prove her wrong by giving up wine for a month; and Bobby's new dog poses some unwanted competition for Andy.

Jules is thrilled for the chance to take care of Travis after his first big break-up. But when Jules discovers the truth about the break-up, she comes to an unwelcome realization about herself. Meanwhile, Sara considers whether Jules threatens her relationship with Grayson and turns to Ellie for guidance; and Andy searches for any resemblance between himself and son Stan.

Jules has difficulty coping when Travis gets ready to leave for college; Andy forms an elaborate plan to deceive Ellie.

As Jules adjusts to living on her own, Grayson unwillingly becomes the new object of her constant attention; Travis turns to Bobby for advice on how to redefine himself at college; and Ellie is determined not to be friends with her new nanny.

Ellie tricks Jules into watching Baby Stan on her own for a day, but Jules is determined to prove how easy it is... especially when she's roped in Grayson to help. Meanwhile, Bobby's given the chance to play golf for free in order to train for his upcoming tournament, as long as he tees off before 6:00 a.m., and Andy volunteers to be Laurie's wingman as she puts herself back out there after her split with Smith.

Travis joins his father and Andy at a professional golf tournament; Jules faces her fear of public humiliation; Ellie and Grayson are impressed by Laurie in a trivia game.

When Travis suffers his first truly broken heart, Jules and Bobby are at a loss as to how to help him. Meanwhile, Grayson stands up to Jules when she tries to tell him what to do, and Ellie turns to Laurie for support when Andy's overly flirty sister-in-law, comes to visit.

Travis wants to take Jules and Grayson's wedding pictures, but Jules, who wants everything to be perfect for her second wedding, isn't so sure; meanwhile Bobby wants to get serious with Angie, but does she feel the same way?

It's the first week of marriage for Grayson and Jules, but when Grayson doesn't know the rules, he soon becomes Jules' "coffee and wine bitch." After Travis' 21st birthday, Bobby tries to make up for lost time by teaching him lessons about being a man. And Ellie and Laurie try to pull Jules out of her depression when Grayson refuses to apologize for what he did in her dream.

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.

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.

When Grayson helps Andy with his tryouts for a new best friend, Jules and Ellie step in to run the bar. But they soon find it's harder than they thought. And Travis and Laurie spend their first weekend alone with Baby Bobby.

Seeing that Andy is unprepared for his upcoming job interviews, Jules agrees to coach him through it. Ellie needs a place to escape since Andy is home all the time, so she goes to Bobby's boat, only to find that Grayson beat her to it. Meanwhile, Travis and Laurie encourage Tom to date ... with disastrous results.

After a hurricane floods the gym of a local high school, Jules volunteers Gray's Pub as a venue for their prom, with the gang ready to serve as chaperones. Jules and Laurie try to have an amazing night, but Laurie isn't feeling it. Andy and Ellie try to stop a gang of bullies. And Travis and Grayson help their high school counterparts win a girl.

Jules tries to read a book for the first time; Grayson tries to remember what his friends say.