Jules Cobb is a mom in her forties facing the often humorous challenges, pitfalls and rewards of life's next chapter. Along for the journey is her son, her ex-husband, her husband/neighbor and her friends who together make up her dysfunctional, but supportive and caring extended family... even if they have a funny way of showing it sometimes.
Jules agrees to stop drinking wine during Laurie's pregnancy, but the rest of the gang doesn't agree, so Tom opens up his garage as a speakeasy. Meanwhile, Grayson prepares Travis for fatherhood with the help of a baby pig.
Jules is overprotective when Chick wants to go to his Civil War reenactment. Bobby considers a job opportunity in another state. Travis hates Laurie's choices for baby names and needs Ellie to destroy them.
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.
Grayson makes a reservation at the hottest restaurant in town, and he and Jules are determined to make it despite constant obstacles. Andy rents a special costume for Stan's birthday, but he has trouble getting it off. And Ellie starts ghost tweeting for Laurie, eventually getting lost in her new character.
Jules sees that Travis is struggling financially, so she lends him money that he uses to start a new business. Ellie takes Andy on a revenge mission after he loses his mayorship. And Grayson fills in as a music teacher at Stan's school.
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.
When Jules finds a bag of unusual items Grayson's been hiding, she goes on a mission to learn his secret. Andy talks Travis into using a baby gift for himself and Ellie can't stand that Laurie is treating Baby Bobby like an accessory.
Jules tries to set her father up with Grayson as a best friend; a cool mom group.
Jules' dinner guests aren't exactly who she expected; staking out a cupcake thief; Tom's patient.
Jules tries to read a book for the first time; Grayson tries to remember what his friends say.
Everyone pitches in to help Tom with his new crush with disastrous results.
Grayson tries to prevent Jules from running her birthday; everyone experiences major life changes.