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.

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 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.

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.

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.