Original air date: 10/02/2019 Runtime: 21:33 min. Will feels like everything is changing as Sophie returns home from camp a seemingly different person, and as he loses out on being room parent to Douglas. Meanwhile, Miggy gets a new temp job at Angie's law firm to help him earn more money to go toward Jack's preschool costs, but he ends up discovering he may like the position more than anyone expected.
Original air date: 10/09/2019 Runtime: 21:34 min. Angie is sent 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.
Original air date: 10/23/2019 Runtime: 21:34 min. Will is pumped to become the coach of Sophie's soccer team in order to spend more time with his daughter, especially since she has been distant recently. However, his intentions to focus on Sophie and teach the team that you don't need to win to have fun slowly shift once he realizes he has a secret weapon on his team: Rory. But allowing Rory on the team also means that Will must keep Rory’s secret. Meanwhile, Douglas and Angie attempt to navigate what their friendship looks like now that they are roommates for the foreseeable future.
Original air date: 10/30/2019 Runtime: 21:34 min. 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 as he attempts 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.
Original air date: 11/20/2019 Runtime: 21:34 min. When Will gets busy cooking Thanksgiving dinner at Douglas' home, he asks Angie to keep his girlfriend, Tracy, company. 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.
Original air date: 12/11/2019 Runtime: 21:34 min. 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. Meanwhile, 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.
Original air date: 01/08/2020 Runtime: 21:34 min. 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.
Original air date: 01/15/2020 Runtime: 21:34 min. 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.
Original air date: 01/22/2020 Runtime: 21:34 min. 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 professional failure.
Original air date: 02/12/2020 Runtime: 21:34 min. 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.
Original air date: 04/22/2020 Runtime: 21:34 min. 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.
Original air date: 04/29/2020 Runtime: 21:34 min. 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 a little too much love.