The kids are away for the summer, and the gang looks forward to their freedom; Angie obsesses over writing the world's longest email to her ex; Douglas inexplicably ghosts Poppy on their first date.
Will feels like everything is changing as Sophie returns home from camp a seemingly different person. Miggy gets a new temp job at Angie's law firm to help him earn more money to go toward Jack's preschool costs.
Angie goes into a tailspin when her long-absent ex-boyfriend Derek suddenly appears on her doorstep; Angie asks Will and Miggy for help because, despite his faults, she can't resist Derek; Douglas and Poppy try for a romantic second date.
After a house incident leaves Graham in fear of staying in his and Angie's home, Angie enlists Will to help her get the house back together; however, there is a hiccup in the plan as Angie discovers a possum on the loose that she has to deal with. Meanwhile, Poppy discovers that Douglas is lying to her about a weekly poker game he must attend, as he participates in a weekly widow's support group instead, causing Poppy to get a little jealous of his emotional vulnerability with the women in his support group.
Will is excited to become the coach of Sophie's soccer team; Douglas and Angie attempt to navigate what their friendship looks like now that they are roommates for the foreseeable future.
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.
Angie's one-night stand turns out to be connected to the group in an unexpected way; Douglas is forced to confront some family issues with a little help from Poppy; Will attempts to teach Miggy how to work on his disciplining skills as a parent.
When Will gets busy cooking Thanksgiving dinner at Douglas's home, he asks Angie to hang out with Tracy Freeze. Angie reluctantly does so, only to realize that Tracy is actually wonderful, except for a secret she's keeping from Will. Meanwhile, Miggy shows up to Thanksgiving dinner with the kids' teacher, Ms. Pronstroller, as his date, and he enlists Douglas' assistance in helping them form an in-person connection, given all of their previous communication has been via texts, DMs and memes.
When Graham brings Douglas' box of 1950s Playboy magazines for show and tell, Angie fears she is a bad mom and knows she has to give "the talk" to Graham. However, Graham has other plans and asks to hear about it from Will and Douglas, which brings out Will's own insecurities when he discovers some kept secrets about his own father's relationships. Meanwhile, Poppy tries to become closer with the twins by helping them discover their individual personalities.
When Graham writes a letter to Santa asking for either a white Christmas or to meet his father, Angie goes on a mission to find snow in Southern California with the help of Will and Sophie. After Rory, Emma, and Amy find out that Poppy and Douglas are romantically involved, the kids use this knowledge to their advantage to guilt their parents into buying them more Christmas presents.
After Will's parents confess that they are inspired by his relationship, which they think is with Angie, Will and Angie must pretend to be a couple for the night in order to keep them from seriously considering divorce. Meanwhile, Douglas steps up to the boyfriend plate and offers to help Poppy with errands, only for her to discover how much she actually likes having time off; and the kids give Tony a makeover to ease his broken heart.
Struggling with unexpected news from Ron's new wife, Sharon, Poppy uses an adventure with Angie to help distract herself from facing her emotions. Meanwhile, Sophie takes on Hilltop, protesting leaving Pete the parrot at school over the three-day weekend, causing Will and Douglas to clash over their stances on activism.
After Angie decides it's finally time for Graham to meet his dad, Derek, 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.
While Graham joins Derek at Ratso's for a day of father-and-son bonding, a jealous Angie enlists Douglas to help her make sure they don't bond too much. The twins and Rory eat all the food in Douglas' house to save his life, and Poppy and Miggy try to help Will with a dating situation named "Kay", only to have it backfire.
It's Valentine's Day! Will and Angie have reunited to help run the student-parent dinner at Hilltop, where the kids are serving up questionable meals to paying customers. Meanwhile, Big Red is back in town and Douglas is worried about how Poppy will react.
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.
Angie uses Sophie as bait to get time with her crush Colin by setting up Sophie and Percy, Colin's son, on a playdate at Angie's house. Meanwhile, Poppy and Douglas navigate Douglas' first night sleeping at Poppy's house, which doesn't go as expected; and Graham and Will go on a bro-date of their own to the pizza parlor.