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.

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.

Angie is sent into a tailspin when her long-absent ex-boyfriend Derek, Graham's father, suddenly appears on her doorstep. She asks Will and Miggy for help because, despite his faults, she can't resist Derek. Meanwhile, 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 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.

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.

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.

When Will gets busy cooking Thanksgiving dinner at Douglas’ 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. 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.

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.

Luchando con noticias inesperadas de la nueva esposa de Ron, Sharon, Poppy utiliza una aventura con Angie para ayudar a distraerse de enfrentar sus emociones. Mientras tanto, Sophie se enfrenta a Hilltop, protestando por dejar a Pete el loro en la escuela durante el fin de semana de tres días, lo que hace que Will y Douglas se enfrenten por sus posturas sobre el activismo.

Después de que Angie decide que finalmente es hora de que Graham conozca a su padre, Dere, la enfermedad invade la casa. Derek se ve obligado a intervenir y ayudar o regresar a su camioneta. Mientras tanto, cuando Sophie escucha algunas noticias importantes sobre Will y Tracy, se encarga de intervenir; y los gemelos enfrentan su primer fracaso profesional.

Mientras Graham se une a Derek en Ratso's para un día de unión de padre e hijo, una Angie celosa recluta a Douglas para ayudarla a asegurarse de que no se unan demasiado. Los gemelos y Rory comen toda la comida en la casa de Douglas para salvar su vida, y Poppy y Miggy intentan ayudar a Will con una situación de citas llamada "Kay", solo para que no funcione.

¡Es el día de San Valentín! Will y Angie se han reunido para ayudar a organizar la cena entre padres y estudiantes en Hilltop, donde los niños sirven comidas cuestionables a los clientes que pagan. Mientras tanto, Big Red está de vuelta en la ciudad y Douglas está preocupado por cómo reaccionará Poppy.

Después de que aumenta la renta en Winebrary, la pandilla interviene a su manera para ayudar a resolver el nuevo problema financiero de Poppy, cada uno aprendiendo una valiosa lección en el proceso.

Angie usa a Sophie como cebo para pasar tiempo con su enamorado Colin al organizar a Sophie y Percy, el hijo de Colin, en una cita de juegos en la casa de Angie. Mientras tanto, Poppy y Douglas navegan la primera noche de Douglas durmiendo en la casa de Poppy, que no sale como se esperaba; y Graham y Will van a una cita por su cuenta a la pizzería.

Cuando Sharon se pone de parto, Poppy y la pandilla se acercan para ayudarla a llegar al hospital, contando cada una de sus propias historias de nacimiento para ayudarla a distraerla de la ausencia de Ron.

Will resuelve una situación difícil después de enterarse de algo sobre el nuevo novio de Angie, Colin, que ella no querrá escuchar. Mientras tanto, Poppy y Douglas luchan por verse cara a cara sobre su futuro, y los niños están solos en casa por primera vez con Graham a cargo.

Angie intenta ayudar a Poppy a superar su situación con Douglas, solo para ser confrontada por el hecho de que podría tener sentimientos por Derek nuevamente. Mientras tanto, Will se distrae de pensar en Angie sofocando a Douglas con demasiado amor y apoyo, haciéndole buscar consuelo en el último lugar donde esperaba encontrarlo.

Con Graham y Sophie en el campamento espacial Lance Bass, Angie decide pasar el verano en Barstow con Derek, dejando a Will tramando una forma de detenerla. Mientras tanto, Rory y los gemelos intentan poner celosos a Poppy y Douglas con el objetivo de volverlos a juntar.

Angie lucha por recordar los eventos de una noche llena de vino con Will, mientras Poppy secretamente anima a Will a compartir sus verdaderos sentimientos. Mientras tanto, Derek llega para reunir a Angie y sus pertenencias, mientras que Rory y Miggy se alistan para encontrar a un chico atractivo para subarrendar la casa.