After seeing the way Douglas and the twins are barely affected by the death of their guinea pig, Pickle, Poppy encourages Douglas to stop repressing his and the twins' feelings. After seeing how close Graham and Will are becoming, Angie gets jealous when Graham asks Will to go get a colonoscopy to check on his health, so Angie decides to get one herself.

Will wants to get back together with Mia, but as their relationship progresses, he finds himself having to choose between the "normal" family he's always wanted and the new family he's created with Angie, Poppy, Miggy, Douglas and the kids. In order to get Will to come back to his senses about Mia, Angie kicks him off the babysitting grid and fills the spot with Dr. Mark, Douglas' rival dermatologist, much to Douglas' chagrin. Meanwhile, Graham is nervous to compete in the talent show and relies on Will to calm him down when he gets nervous on stage.

In a magical encounter at the Bachelor mansion, Chris Harrison bestows his wisdom on a frustrated Poppy and Angie, attempting to restore their faith in love and happy endings. Meanwhile, Will saves one of the kids at school from playground injury; and Douglas insists Will capitalize on the glow from this heroic act by getting as much attention from women as possible within its 24-hour window.

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.

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.

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.

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 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.

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.

Angie struggles to recall the events of a wine-filled night of packing with Will, while Poppy secretly encourages Will to share his true feelings. Meanwhile, Derek arrives to gather Angie and her belongings, while Rory and Miggy are enlisted to find a hot guy to sublet the house.