By: Quinn Que
Charlie (Luke Macfarlane) is preparing to head into work while Sylvia (Rose Byrne) expresses concern about whether that’s wise after learning about his break-in at the Jeopardy producer’s house. She suggests he see a therapist, but Charlie insists he’s fine and points out that neither of them has needed therapy before, even during Sylvia’s difficult pregnancy and postpartum period. Though Sylvia seems less certain about his assessment, she lets the matter drop.
Will (Seth Rogen) needs transportation to a company retreat being run by his ex-fiancée Jenna (Rachel Rosenbloom). Sylvia reluctantly agrees to drive him but warns that Frances (Sophie Leonard) will be taking the wheel for the first part of the journey since they’re headed to her math competition. During their preparations, Sylvia receives a call from Katie (Carla Gallo) requesting support, so they pick her up along the way.
Katie reveals she’s feeling upset and upstaged because her first ex-husband is expecting a child with his younger new wife. When Will makes critical comments about the situation, he gets yelled at by the women. Frances drops herself off and links up with her bestie. They tell themselves they’re cooler and prettier than everyone there, “not like the other nerds.”
The rest of the group continues on, with Sylvia taking the wheel. As the trip progresses, Will and Katie begin bonding over their shared experience as divorcees, leaving Sylvia feeling excluded from their connection.
Meanwhile, at the office, Charlie experiences a barely contained, inaudible panic attack during a meeting and excuses himself to the restroom. In his distressed state, he hallucinates someone mocking him from the bathroom stalls, but discovers no one is there except a shy person using the facilities for a #2. Charlie is beside himself.
The road trip group stops at Red’s Tavern, a restaurant-slash-bar that Will greatly admires, calling it legendary in the brewing industry. Their conversation turns to home life, with Sylvia arguing that hers is better than theirs because she and Charlie maintain stability. Will counters by pointing out that Charlie is essentially going through a mental episode related to the Jeopardy incident, which Sylvia continues to deny.
Back on the road, Will reveals he’s packed a giant stuffed penguin as a peace offering for Jenna, explaining that penguins were their favorite animal as a couple. The women insist this gesture is too weird and attempt to throw the penguin out of the car. As Katie and Will wrestle over the stuffed animal in the backseat, it explodes, and Sylvia, distracted by the commotion, nearly crashes the vehicle. Her windshield sustains damage in the process.
At a nearby mechanic shop, the staff attempt to bamboozle and strong-arm Sylvia for money, refusing to let her drive away unless she waits two days and pays at least four thousand dollars in upfront costs. Sylvia calls Charlie for legal advice, but before she can explain the situation, he admits he had a panic attack and went home early from work. Unable to burden him with additional problems, she simply tells him she loves him and will be home soon.
Will and Katie encourage Sylvia to be the strong one in the relationship for once, since Charlie currently can’t fulfill that role. Initially struggling to assert herself with the intimidating mechanics, Sylvia decides to scare them by further damaging her own windshield with a fire extinguisher, completely destroying it. Shocked by her seemingly erratic behavior, the mechanics call her crazy and allow her to leave.
The group continues their journey in a car with no windshield, wearing safety goggles for eye protection. They make another restaurant stop, where Will stares at the torn-up penguin and realizes he can’t go to the retreat. He calls corporate to resign effective immediately and announces his decision to purchase Red’s Tavern for its brewing equipment instead.
Katie agrees to help Will handle the process of packing up the brewing stuff and helping set up his new business venture. When Sylvia offers to stay and help as well, both Will and Katie insist she should return home to Charlie, who needs her support more than they do.