Will Cooper has been so focused on raising his daughter, Sophie, he's lost sight of who he is as a man and has headed deep into the parental vortex. When the other single parents - Angie, Douglas, Poppy and Jake - at his daughter's school see just how far down the rabbit hole of PTA, parenting and princesses Will has gone, they band together to get him out in the world and make him realize that being a great parent doesn't mean sacrificing everything about your own identity.
Douglas is stuck hosting the kids' Saturday sleepover, and Will uses this as an opportunity to try to bond with Douglas, something he hasn't been able to do before. Angie and Graham both struggle with their own fear of sleepovers - Graham is worried to stay the night without his mom and not in his own house, and Angie is worried to sleep over with her man friend Owen. Meanwhile, Poppy helps Miggy come up with potential job ideas in order to help him become more responsible.
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.
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.
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.
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.
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 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.
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.
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 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 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 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.
Douglas discovers that Amy is a math genius and is overwhelmed with how much time he has to spend to treat his daughters as individuals for the first time ever; this eventually leads to Emma moving into their private shed to get some space from Amy. Meanwhile, Graham makes a new friend at school, causing Angie to have to spend time with his new friend's mom, Nora, to Angie's chagrin. After Angie meets Nora in person and enjoys spending time with her, Poppy starts to grow jealous of Angie's newfound friendship.
Douglas agrees to babysit the kids on Valentine's Day, but when Graham finds himself in a Valentine's Day emergency and Big Red shows up unannounced, Douglas and Big Red band together to help Graham. Meanwhile, Will and Miggy celebrate "Palentine's Day" together - a day honoring the love of two friends - but when they run into Angie at her second job, they help her finish her deliveries so she can be with Owen on Valentine's Day.
When Poppy's ex-husband, Ron, gets serious with his latest girlfriend, Poppy has to deal with the reality of another woman helping to raise her kid. The secret gets out that Sophie has a crush on Graham, which causes a stir not only in the first-grade classroom, but also between Angie and Will. Meanwhile, Miggy gets cold feet after asking Douglas to remove his tattoo of Zara's initials, and Douglas has to help him realize that his relationship with Zara is officially over.
Seeing that baby Jack is about to walk for the first time, Miggy feels old and tries to recapture his youth by throwing an epic party. When the party doesn't go as expected, he insists that Poppy and Douglas stick around to help him. Angie's boyfriend, Owen, meets Graham for the first time, which doesn't go as well as they had hoped. When Will gets an opportunity to do the weather at 10:00 p.m., Rory tags along and causes drama on the set.
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.
When no one bids on "Lunch with KZOP's Will Cooper" at the school auction, Poppy and Sophie scheme together to recruit Dr. Biscuits to bid on Will and play the role of his No. 1 fan. Meanwhile, Douglas attempts to teach a reluctant Angie how to cut back on extra spending and become more fiscally responsible.
To celebrate Angie's 30th birthday, Will throws a big party recreating Ozzfest, which Angie missed in her 20s. When Angie assumes Owen planned it for her, awkward encounters ensue. Meanwhile, Douglas takes Graham shopping to help him find the perfect gift for his mom, Angie, for her birthday, but a distracted Douglas results in Graham buying a not-so-on-point gift.