Robert is distracted by the laughter coming from Jenny’s mom, Linda, and her much-younger boyfriend, Evan, in the next room. Robert and Evan have an awkward hallway encounter, leaving Evan retreating to his room. Jenny is surprised her mom never mentioned Evan’s age, but Jenny’s husband Mike notes she looks happy.
At breakfast, Linda reveals she and Evan met skydiving. When Max and his dad Mike plan to build a booth for the holiday stroll, Evan offers to help, irritating Robert. Max suggests Robert and Evan work together, but tensions rise. Later, Linda admits she hid the age gap, fearing Jenny wouldn’t give them a chance. She wants mother-daughter time, but Jenny’s busy with work.
While building the booth, Robert and Evan blame each other when it breaks and they trade age insults. To lighten the mood, Jenny suggests broomball, where Robert aggressively knocks Evan down, despite being on the same team. Linda expects Robert to apologize, so he brings Evan a sandwich. They bicker until discovering a shared love for soccer, bonding over the meal.
Everyone is shocked to hear them laughing together. At dinner, as the family winds down, Robert and Evan head to a bar, annoying Linda. Over drinks, they admit they misjudged each other. Robert feels aged out of his career, while Evan assures him he still has it—especially when a woman at the bar sends Robert a drink. Encouraged by Evan, Robert gets her number.
Meanwhile, Max confides in Mike that Annie has been acting differently. Mike tries to reassure him by saying he understands it’s difficult when relationships change.
The next morning, Robert and Evan are up early, dancing in the garage while finishing the booth. Jenny and Mike joke that Evan is basically a younger Robert. Robert urges Jenny to have more fun, and she asks Linda to help wrap gifts. Evan asks Robert for gift advice, and Robert suggests a special lamp. Evan returns the favor by giving Robert a makeover for his date with Gail, the woman from the bar.
Linda critiques Jenny’s gift for Mike but is speechless when she sees Robert’s makeover and hears about his date. When she opens Evan’s gift—a lamp projecting the Northern Lights—she’s touched, realizing Robert helped pick it.
At the holiday stroll, Max hasn’t seen Annie and worries about her. Gail arrives, impressed by the booth, and Robert introduces her to the family—including his ex-wife. Linda overshares about their marriage until Evan pulls her away, but she later thanks Robert for choosing her gift, sharing a heartfelt moment.
Evan grows suspicious of Linda and Robert’s bond. During an escalating tense conversation, Evan accidentally trips Robert, injuring his knee. Linda scolds them, and Evan demands to know what’s going on. Both deny anything romantic, but Linda storms off with Jenny.
Robert and Evan apologize for interfering in each other’s lives. Robert fears he blew it with Gail, but Evan encourages him.
Meanwhile, Linda reflects on her past love for Robert, and Jenny wonders if she still has feelings for him.
Back home, Linda and Jenny are stunned to find Gail tending to Robert.