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 Douglas to wear a silly costume; Angie struggles to tell her boss that she needs to leave work to be with her son on Halloween.
Will hits it off with Angie and Graham's pediatrician, but Angie worries he'll ruin Graham's chances of getting on the list for the flu vaccine; Douglas gets sick, and while delirious with a fever, he accidentally reveals to Rory that he likes Poppy.
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 try to appeal to the drama teacher to make changes; Will lies to Sophie about Dr. Dewan.
Angie enlists Will's help in finding a last-minute gift for Owen; Graham begins to doubt the existence of Santa Claus; Douglas invites Poppy to compete in a series of cutthroat Christmas-themed competitions.
Will decides to audition for his dream job as an on-camera weatherman; 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.
When Will's ex shows up unexpectedly for Sophie's birthday, Will gets frustrated that she undermines his rules; 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 must choose which family he wants to pursue; Angie kicks Will off the babysitting grid and fills the spot with Dr. Mark, Douglas' rival dermatologist; Graham is nervous about competing in a talent show.
Douglas agrees to baby-sit the kids on Valentine's Day; Douglas and Big Red band together to help Graham with his Valentine's Day emergency; Will and Miggy help Angie finish her deliveries so she can be with Owen on Valentine's Day.
When Poppy's ex-husband gets serious with his latest girlfriend, Poppy has to deal with the reality of another woman helping to raise her kid; Miggy gets cold feet after asking Douglas to remove his tattoo of Zara's initials.
Seeing that baby Jack is about to walk for the first time, Miggy tries to recapture his youth by throwing an epic party; when the party doesn't go as expected, he insists that Poppy and Douglas help him; Angie's boyfriend meets Graham.
In a magical encounter at the Bachelor mansion, Chris Harrison bestows his wisdom on a frustrated Poppy and Angie; Will saves one of the kids at school from a playground injury; Douglas insists Will capitalize on the glow from this heroic act.
When no one bids on "Lunch with KZOP's Will Cooper" at the school auction, Poppy and Sophie scheme to recruit Dr. Biscuits to bid on Will and play the role of his biggest fan; Douglas attempts to teach Angie how to cut back on extra spending.
Will starts to date someone new and ditches his TV-watching plans with Angie; Poppy and Douglas bond over working on Rory's class president campaign until Poppy finds out about some of Douglas' shady campaign tactics.
Will forgets to send in Sophie's deposit for space camp, so he must woo the owner of the company in order to get her spot at camp back; Poppy deals with unwanted old feelings for her ex Ron as she helps him plan his wedding.
After learning that Angie's ex lives near Space Camp, Will convinces Angie to confront him about leaving her when she was pregnant; Poppy internally struggles with who she truly has romantic feelings for.