Grayson tries to prevent Jules from running her birthday; everyone experiences major life changes.
Everyone pitches in to help Tom with his new crush with disastrous results.
In the 100th episode, the gang takes on new personal challenges: Jules tries to read a book for the first time, Grayson tries to listen to his friends and remember what they have to say, and Andy tries to keep his hand out of a place it doesn't belong.
Jules invites Chick and his new girlfriend to a dinner party, but her guests aren't exactly who she expected. Travis and Laurie stake out a cupcake thief, and Andy and Ellie try to figure out who Tom's celebrity patient is.
Fearing that her dad, Chick, is lonely, Jules tries to set him up with Grayson as a best friend. Laurie helps Andy fit in with a cool mom group and Travis and Ellie open up to each other in the Winebulance.
Jules finds a bag of peculiar items Grayson has been hiding; Travis uses a baby gift for himself.
A hurricane floods a local high school gym; Jules volunteers Gray's Pub as a venue for their prom.
Jules agrees to coach Andy through his interviews; Ellie goes to Bobby's boat to escape Andy.
Jules lends Travis money to start a new business; Ellie takes Andy on a revenge mission; Grayson fills in as a music teacher at Stan's school.
Jules and Grayson are determined to make it to their reservation at the hottest restaurant in town; Andy has trouble with a costume he rented for Stan's birthday; Ellie starts ghost-tweeting for Laurie and gets lost in a new identity.
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.
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.
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.