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.

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.

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.

When Sharon goes into labor, Poppy and the gang step up to help her get to the hospital, telling each of their own birth stories to help distract her from Ron’s absence.

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.

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.

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.

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 decides to audition for his dream job as an on-camera weatherman, but in order to succeed, he needs a little help from Miggy, Poppy and Sophie to hone in on the perfect persona. Meanwhile, after Angie discovers that Graham has the word "FARTS" written on his forehead in permanent marker, she goes on a mission to obtain an apology from the responsible parties - Emma and Amy - and unfortunately Douglas does not provide much help.

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.

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 Graham brings Douglas’ box of 1950s Playboy magazines for show and tell, Angie fears she is a bad mom and knows she has to give “the talk” to Graham. However, Graham has other plans and asks to hear about it from Will and Douglas, which brings out Will’s own insecurities when he discovers some kept secrets about his own father’s relationships. Meanwhile, Poppy tries to become closer with the twins by helping them discover their individual personalities.

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.

After rent on the Winebrary goes up, the gang all chip in in their own ways to help solve Poppy's new financial problem, each learning a valuable lesson in the process.

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.

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.