A bunch of single parents band together to help a 30-something guy who's been so focused on raising his 7-year-old daughter that he's sacrificed his personal life.
With Graham and Sophie away at Lance Bass Space Camp, Angie decides to spend the summer in Barstow with Derek, leaving Will plotting a way to stop her. Meanwhile, Rory and the twins attempt to make Poppy and Douglas jealous with the goal of getting them back together.
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. 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.
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.
Angie struggles to recall the events of a wine-filled night of packing with Will, while Poppy secretly encourages Will to share his true feelings. Meanwhile, Derek arrives to gather Angie and her belongings, while Rory and Miggy are enlisted to find a hot guy to sublet the house.Watch Now:AmazoniTunes
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.Watch Now:AmazoniTunes
After learning that Angie's ex, Derek, lives near Space Camp, Will convinces Angie to confront him about leaving her when she was pregnant, which results in a rowdy and awkward encounter between the three of them. Meanwhile, Poppy internally struggles with who she truly has romantic feelings for.Watch Now:AmazoniTunes
Angie attempts to help Poppy through her situation with Douglas, only to be confronted by the fact that she might have feelings for Derek again. Meanwhile, Will distracts himself from thinking about Angie by smothering Douglas with a little too much love and support, causing him to look for comfort in the last place he expected to find it.
Douglas discovers that Emma 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 Amy moving into their private shed to get some space from Emma. 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.
When Graham brings Douglas' box of 1950s Playboy magazines for show-and-tell, Angie knows she has to give "the talk'' to Graham; Poppy tries to become closer with the twins by helping them discover their individual personalities.
Struggling with unexpected news from Ron's new wife, Sharon, Poppy uses an adventure with Angie to help distract herself from facing her emotions. Meanwhile, Sophie takes on Hilltop, protesting leaving Pete the parrot at school over the three-day weekend, causing Will and Douglas to clash over their stances on activism.
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.
On Valentine's Day, Will and Angie reunite to help run the student-parent dinner at Hilltop, where the kids are serving up questionable meals to paying customers; Big Red is back in town and Douglas is worried about how Poppy will react.
Will feels like everything is changing as Sophie returns home from camp a seemingly different person. Miggy gets a new temp job at Angie's law firm to help him earn more money to go toward Jack's preschool costs.
Will works through a difficult situation after he learns something about Angie's new boyfriend that she won't want to hear; Poppy and Douglas struggle to see eye-to-eye about their future; the kids stay home alone for the first time.
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.
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.
After Angie decides it's finally time for Graham to meet his dad, Derek, sickness overtakes the household. Derek is forced to either step in and help or head back out to his van. Meanwhile, when Sophie overhears some big news about Will and Tracy, she takes it upon herself to intervene; and the twins face their first professional failure.
Angie is sent into a tailspin when her long-absent ex-boyfriend Derek suddenly appears on her doorstep; Angie asks Will and Miggy for help because, despite his faults, she can't resist Derek; Douglas and Poppy try for a romantic second date.
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.
The kids are away for the summer, and the gang looks forward to their freedom; Angie obsesses over writing the world's longest email to her ex; Douglas inexplicably ghosts Poppy on their first date.Watch Now:AmazoniTunes
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.
While Graham joins Derek at Ratso's for a day of father-and-son bonding, a jealous Angie enlists Douglas to help her make sure they don't bond too much. The twins and Rory eat all the food in Douglas' house to save his life, and Poppy and Miggy try to help Will with a dating situation named "Kay," only to have it backfire.
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.