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.

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.

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.

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.

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.

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.

Angie is sent into a tailspin when her long-absent ex-boyfriend Derek, Graham's father, suddenly appears on her doorstep. She asks Will and Miggy for help because, despite his faults, she can't resist Derek. Meanwhile, Douglas and Poppy try for a romantic second date.

After a house incident leaves Graham in fear of staying in his and Angie’s home, Angie enlists Will to help her get the house back together; however, there is a hiccup in the plan as Angie discovers a possum on the loose that she has to deal with. Meanwhile, Poppy discovers that Douglas is lying to her about a weekly poker game he must attend, as he participates in a weekly widow’s support group instead, causing Poppy to get a little jealous of his emotional vulnerability with the women in his support group.

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 the 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 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.

The kids are away for the summer, and the gang looks forward to their freedom. But three months later, it looks like summer is a bust with Will doing all the things on the "Angie and Will's List of Summer Fun" with Tracy Freeze; Angie obsessing over writing the world's longest email to her ex; and Douglas inexplicably ghosting Poppy on their first date.

Will is pumped to become the coach of Sophie's soccer team in order to spend more time with his daughter, especially since she has been distant recently. However, his intentions to focus on Sophie and teach the team that you don't need to win to have fun slowly shift once he realizes he has a secret weapon on his team – Rory – but allowing him on the team means Will must keep a certain secret about Rory. Meanwhile, Douglas and Angie attempt to navigate what their friendship looks like now that they are roommates for the foreseeable future.

Will works through a difficult situation after he learns something about Angie’s new boyfriend, Colin, that she won’t want to hear. Meanwhile, Poppy and Douglas struggle to see eye-to-eye about their future, and the kids are home alone for the first time with Graham in charge.

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 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 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.

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.

After Will realizes he forgot to send in Sophie's deposit for space camp, he must woo the owner of the company, Lance Bass, in order to get her spot at camp back. Meanwhile, the twins' grandmother shows up wanting more time with Amy and Emma during the summer, causing Douglas to spin; and Poppy deals with unwanted old feelings for her ex Ron as she helps him plan his wedding.

Will feels like everything is changing as Sophie returns home from camp a seemingly different person and as he loses out on being room parent to Douglas. Meanwhile, Miggy gets a new temp job at Angie’s law firm to help him earn more money to go toward Jack’s preschool costs, but he ends up discovering he may like the position more than anyone expected.

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.

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.

It's Valentine’s Day! Will and Angie have reunited to help run the student-parent dinner at Hilltop, where the kids are serving up questionable meals to paying customers. Meanwhile, Big Red is back in town and Douglas is worried about how Poppy will react.