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.

Despite Grayson's warning, a curious Jules reads the speech without permission and is left crushed when she finds she's not been acknowledged. Meanwhile, Ellie uncharacteristically does something nice for Laurie, and Bobby tries to restrain himself from embarrassing Travis on his big day.

Bobby struggles with the reality of Jules being in a relationship with Grayson. Jules has issues with her new psychiatrist when she discovers the truth behind her methods.

When Grayson doesn't share Jules' sadness on a series of unfortunate but accidental events, she questions whether they're meant to be together.

Meanwhile, Travis' new girlfriend throws Bobby off his golf game, and Ellie gets upset with Andy when he uses their joke on Laurie.

When Travis abruptly moves to Hawaii, the gang go after him and decide to spend their vacation there too. As Jules struggles with Travis' choice, Grayson tells her he's keen on having kids. Meanwhile, Bobby acts as Ellie and Andy's vacation surrogate, and Laurie hatches a plan to lure Travis back home.

Jules is miffed when Grayson (who has an ulterior motive) calls her "predictable"; Ellie frets that little Stan is turning into a "devil child," or even worse, could grow up to be like Laurie; and Travis likes his new off campus housing, until Bobby tries to convince him to take dog Travis in.