Will, a 30-something guy, has been so focused on raising his daughter that he’s lost sight of who he is as a man. When the other single parents 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 dating world and make him realize that being a great parent doesn’t mean sacrificing everything about your own identity.

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.

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.

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.

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.

Angie and Will dive headfirst into binge-watching a show called "JOUST!" together, but when Will starts to date someone new and ditches his TV-watching plans with Angie for time with his new love interest, Angie grows frustrated. Meanwhile, Poppy and Douglas bond over working on Rory's class president campaign until Poppy finds out about some of Douglas' shady campaign tactics.