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.
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.
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 him on the team means Will must keep a certain secret about Rory. Meanwhile, Douglas and Angie attempt to navigate what their friendship looks like now that they are roommates for the foreseeable future.
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.
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.
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.
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.
After learning that Angie’s ex, Derek, lives near Space Camp, Will convinces Angie to confront him about leaving her when she was pregnant, which results in a rowdy and awkward encounter between the three of them. Meanwhile, Poppy internally struggles with who she truly has romantic feelings for.
After Will realizes he forgot to send in Sophie’s deposit for space camp, he must woo the owner of the company, Lance Bass, in order to get her spot at camp back. Meanwhile, the twins’ grandmother shows up wanting more time with Amy and Emma during the summer, causing Douglas to spin; and Poppy deals with unwanted old feelings for her ex Ron as she helps him plan his wedding.