Will encourages Angie to rediscover her passion for heavy metal music by taking a guitar class, and in turn, Angie insists that Will get back in the field covering weather by driving both of them into a storm. Meanwhile, the rest of the gang explore their romantic passions as Douglas pursues his crush on Big Red with the help of Miggy, and Poppy feels an instant connection with a dreamy musician.

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.

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.

To celebrate Angie's 30th birthday, Will throws a big party recreating Ozzfest, which Angie missed in her 20s; but 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.

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.

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.

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.

It’s Halloween night at Hilltop Elementary and the kids head to the school for a spooky celebration with Douglas. Will struggles with whether he should stay with Sophie at the school party or if he should swing by his girlfriend Tracy Freeze’s birthday, which results in a stressful night for Will trying to do both. Meanwhile, Poppy and Angie throw a Halloween party for teens at Douglas’ house in order to try to prove to themselves that they are cool moms.

When Will gets busy cooking Thanksgiving dinner at Douglas’ home, he asks Angie to hang out with Tracy Freeze. Angie reluctantly does so, only to realize that Tracy is actually wonderful, except for a secret she’s keeping from Will. Meanwhile, Miggy shows up to Thanksgiving dinner with the kids’ teacher, Ms. Pronstroller, as his date, and he enlists Douglas’ assistance in helping them form an in-person connection, given all of their previous communication has been via texts, DMs and memes.

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. Meanwhile, 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.

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.

After Angie decides it’s finally time for Graham to meet his dad, Dere, 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.

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.