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.
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.
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.
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.
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.
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.
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.
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.
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.
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.