Seeing that baby Jack is about to walk for the first time, Miggy feels old and tries to recapture his youth by throwing an epic party. When the party doesn't go as expected, he insists that Poppy and Douglas stick around to help him. Angie's boyfriend, Owen, meets Graham for the first time, which doesn't go as well as they had hoped. When Will gets an opportunity to do the weather at 10:00 p.m., Rory tags along and causes drama on the set.

Angie and Will dive headfirst into binge-watching a show called "JOUST!" together, but when Will starts to date someone new and ditches his TV-watching plans with Angie for time with his new love interest, Angie grows frustrated. Meanwhile, Poppy and Douglas bond over working on Rory's class president campaign until Poppy finds out about some of Douglas' shady campaign tactics.

The kids are away for the summer, and the gang looks forward to their freedom. But three months later, it looks like summer is a bust with Will doing all the things on the "Angie and Will's List of Summer Fun" with Tracy Freeze; Angie obsessing over writing the world's longest email to her ex; and Douglas inexplicably ghosting Poppy on their first date.

It’s Halloween night at Hilltop Elementary and the kids head to the school for a spooky celebration with Douglas. Will struggles with whether he should stay with Sophie at the school party or if he should swing by his girlfriend Tracy Freeze’s birthday, which results in a stressful night for Will trying to do both. Meanwhile, Poppy and Angie throw a Halloween party for teens at Douglas’ house in order to try to prove to themselves that they are cool moms.

When the smooth-talking ladies' man, Xander, from Angie's one night stand turns out to be connected to the group in an unexpected way, she starts spiraling. Douglas is forced to confront some family issues with a little help from Poppy. Meanwhile, Will attempts to teach Miggy how to work on his disciplining skills as a parent, but Sophie, Rory and Graham make it anything but easy on him.

After Angie decides it’s finally time for Graham to meet his dad, Dere, sickness overtakes the household. Derek is forced to either step in and help or head back out to his van. Meanwhile, when Sophie overhears some big news about Will and Tracy, she takes it upon herself to intervene; and the twins face their first professional failure.

After rent on the Winebrary goes up, the gang all chip in in their own ways to help solve Poppy's new financial problem, each learning a valuable lesson in the process.