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.

Angie enlists Will to help her get the house back together; Poppy discovers that Douglas is lying to her about a weekly poker game he must attend.

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.

The kids head to the school for a spooky Halloween celebration with Douglas; Will has a stressful night trying to do too much; Poppy and Angie throw a Halloween party at Douglas' house 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 confronts some family issues with a little help from Poppy; Will attempts to teach Miggy how to work on his disciplining skills as a parent.

Will gets busy cooking Thanksgiving dinner at Douglas' home; Miggy shows up to Thanksgiving dinner with the kids' teacher, Ms. Pronstroller, as his date, and he enlists Douglas' assistance in helping them form a connection.

When Graham brings Douglas' box of 1950s Playboy magazines for show-and-tell, Angie knows she has to give "the talk" to Graham; 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; Rory, Emma and Amy find out that Poppy and Douglas are romantically involved.

After Will's parents confess to being inspired by his relationship, which they think is with Angie, Will and Angie must pretend to be a couple for the night to keep them from considering divorce; Douglas offers to help Poppy with errands.

Poppy uses an adventure with Angie to help distract herself from facing emotions; Sophie protests 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, sickness overtakes the household; when Sophie overhears some big news about Will and Tracy, she takes it upon herself to intervene; the twins face their first failure.

When 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; Poppy and Miggy try to help Will with a dating situation.

On Valentine's Day, Will and Angie reunite to help run the student-parent dinner at Hilltop, where the kids are serving up questionable meals to paying customers; 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 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; Poppy and Douglas navigate Douglas' first night sleeping at Poppy's house; Graham and Will go to the pizza parlor.

When Sharon goes into labor, Poppy and the gang step up to help her get to the hospital, telling each of their own birth stories to help distract her from Ron's absence.

Will works through a difficult situation after he learns something about Angie's new boyfriend that she won't want to hear; Poppy and Douglas struggle to see eye-to-eye about their future; the kids stay home alone for the first time.

Angie attempts to help Poppy through her situation with Douglas, only to be confronted by the fact that she might have feelings for Derek again; Will distracts himself from thinking about Angie by smothering Douglas with too much love.

With Graham and Sophie away at Lance Bass Space Camp, Angie decides to spend the summer in Barstow with Derek; Rory and the twins attempt to make Poppy and Douglas jealous with the goal of getting them back together.

Angie struggles to recall the events of a wine-filled night of packing with Will; Poppy secretly encourages Will to share his true feelings; Derek arrives to get Angie and her belongings.