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.

Scott Foley gest 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.

When the relationship between Jules and her boyfriend start to heat up, Jules starts to get scared. Meanwhile, Laurie seeks diversion sex with an unsuspecting friend and Andy spills the beans about his big secret.

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.

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

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 and the gang decide Bobby needs some help romancing Angie so they launch "operation kiss-the-girl." Meanwhile, other former "Scrubs" cast turn up, as Ted and the Peons pass through on their way to audition at Disney World.