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 thea 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.
When Will’s ex, Mia, shows up unexpectedly for Sophie’s birthday, Will gets frustrated that she undermines his rules with Sophie. Angie tries to help Will cope by having a fun girls’ night at her place and by giving some co-parenting advice, but Poppy reveals and Will quickly learns that Angie isn’t the best advice giver. Meanwhile, inspired by Mia’s humanitarian work, Miggy and Graham decide to give some items to charity but regret it immediately and seek out help from Douglas to get the items back.
Will decides to audition for his dream job as an on-camera weatherman, but in order to succeed, he needs a little help from Miggy, Poppy and Sophie to hone in on the perfect persona. Meanwhile, after Angie discovers that Graham has the word “FARTS” written on his forehead in permanent marker, she goes on a mission to obtain an apology from the responsible parties – Emma and Amy – and unfortunately Douglas does not provide much help.
When Owen shows up unexpectedly on Christmas Eve with a gift for Angie, she desperately seeks out help from Will finding a present for Owen last minute. While doing so, Angie learns how bad Will is at giving Sophie good Christmas presents, or so it seems. While Graham begins to doubt the existence of Santa Claus altogether, the group worries Miggy may still believe in him. Meanwhile, Douglas invites Poppy, who is dealing with her first Christmas without Rory, to compete in a series of cutthroat Christmas-themed competitions.
Will is thrilled to throw the first-grade parent social so that he can use this event to springboard his anti-smartphone platform to get parents to wait to buy their kids cellphones until eighth grade. He ropes his new love interest, Dr. Dewan, into helping him, but his plan doesn’t work out quite like he had hoped. Douglas offers to have the social at his house so he can exact revenge on his rival dermatologist, Mark, whom Douglas is convinced stole his prized pen.
Will encourages Angie to rediscover her passion for heavy metal music by taking a guitar class, and in turn, Angie insists that Will get back in the field covering weather by driving both of them into a storm. Meanwhile, the rest of the gang explore their romantic passions as Douglas pursues his crush on Big Red with the help of Miggy, and Poppy feels an instant connection with a dreamy musician.
When Graham and Rory are cast in their school’s production of “Grease,” with Graham as the lead and Rory with a lesser known part, Poppy and Angie get involved and try to appeal to the drama teacher, Dr. Biscuits, to make changes. Meanwhile, Will is not ready to tell Sophie that he’s seeing Dr. Dewan, so against his better judgment, he takes Douglas’ advice and lies to Sophie.
Will hits it off with Angie and Graham’s pediatrician, Dr. Dewan, but Angie worries he’ll ruin Graham’s chances of getting on the Mist List for the flu vaccine. Miggy tries to help Will navigate how to handle his situation with Dr. Dewan by giving dating advice. Meanwhile, Douglas gets sick, and while delirious with a fever, he accidentally reveals to Rory that he likes Poppy.
Will is crushed when Sophie wants to tone down Halloween and invites a boy over. Poppy and the twins attempt to convince a reluctant Douglas to wear a silly costume; after he finally puts it on, he meets the woman of his dreams, who he now is sure will not take him seriously. Meanwhile, Angie struggles to tell her boss that she needs to leave work to be with her son on Halloween, leaving Graham’s costume in limbo.
After scolding Miggy for not being able to sleep-train baby Jack, Angie and Douglas engage in a competition to see who can sleep-train the baby in one night. While Angie and Douglas have the baby, Miggy takes over babysitting Graham, Rory, Sophie, Emma and Amy, which results in an impromptu kids’ party. Meanwhile, Poppy teaches Will how to take out his anger on the volleyball court.