Cars, Trains and Motorcycles

Whit, Connie, Eugene, and Wooton pile into a borrowed car for a road trip from Odyssey to Chicago, where Penny's artwork is on display at the Warner Art Gallery until eight o'clock that evening. Penny nearly cried when she learned her friends were coming all that way just for her, so nobody wants to miss it. There's just one complication: Whit has had an emergency tooth extraction that morning, and his pain pills have left him hilariously loopy. He chats with a mailbox, tries to tan his face in the glove box, and attempts to make toast in the air conditioning vents. Wooton's borrowed car brings troubles of its own, since it's foreign, its gauges use the metric system, and most of them don't work anyway. Eugene has planned the schedule down to the second, Wooton has packed a snack supply heavy on gummy worms and popcorn balls, and Connie has brought a bag stuffed with books so she can do homework the whole way.

Trouble starts early. Wooton mistakes the odometer for the fuel readout, the car runs out of gas, and he has to hike to an exit to refill it. Meanwhile a phone call from Katrina, about whether a new guidance counselor is a good fit for Buck, stirs up an old grievance: Connie doubts Eugene's judgment of character because he once set her up on a blind date with Clint, a student from his class. Connie calls it the worst date of her life. Clint mocked her dress, criticized everything about her, and made her feel like she was on a date with "the comments section of a social media post."

When traffic near Chicago grinds to a complete stop, Eugene devises a plan: park the car and take the L train. But the crowd on the platform sweeps the friends apart. Connie and Eugene make it into one car, Wooton lands in the car ahead, and Whit ends up in the car behind, not answering his phone. As Connie and Eugene bicker, a stranger named Sally Dearborne interrupts, introduces herself as a counselor, and offers them relationship help. Told they aren't a couple, she replies that this makes sense because "you two aren't exactly in the same league with each other," then hops off the train, leaving them both stewing over which of them she meant was in the higher league.

Elsewhere on the train, Wooton cheerfully violates the no-small-talk rule of public transit, while a woozy Whit informs a large, intimidating stranger that his tattoo misquotes the book of Revelation. The man, Bruce, growls that his tattoo is a butterfly bearing the name Winnie, his ex-girlfriend. But instead of a fight, a friendship forms: Bruce confesses that when Winnie left, she took all their friends, and he feels completely alone. Whit gently tells him that he himself could never be truly alone, because he has good friends and God watches over him, and he offers to pray for Bruce.

Back in the other car, Connie recounts how Clint made their server cry by docking her tip for every crouton she forgot to leave off his salad. Eugene, examining the details, can only conclude, "That's too many croutons," before finally admitting that Clint is, in plain language, a jerk. When the group's stop arrives, Connie and Eugene reunite with Wooton, but Whit, deep in conversation with Bruce, misses it and rides on. With only minutes left before the gallery closes, the friends split up again. Wooton takes off running the final twelve blocks, Connie and Eugene wait for a rideshare, and Bruce gives Whit a lift on his motorcycle, with Whit boldly telling him to get the hog moving. In the rideshare, Eugene sincerely apologizes. He explains he set up the date because Connie had been studying so hard and deserved a night out. Connie softens, but reminds him that friends have to look out for each other.

Wooton reaches the gallery at 7:56, only to be turned away: on Wednesdays, the gallery is members-only after seven. Whit and Bruce roar up, then Connie and Eugene arrive, and the whole group stands defeated on the sidewalk, certain they've let Penny down. It's Bruce who sets them straight. Whit had dental surgery, Connie had a mountain of homework, Eugene gave up a whole day with his family, and Wooton ran from somewhere he can only guess was Indiana. Penny, Bruce declares, is lucky to have friends like them. Whit agrees that they're all blessed to have one another, and he adds that Eugene's matchmaking blunder came from a place of fondness for Connie, revealing that the pain pills never made him deaf.

Then Penny calls and tells Wooton to look up. She's waving from a window above, and the display is visible through the glass. Bruce hoists Wooton onto a ledge for a reunion with his wife, and Eugene and Connie trade final apologies, with Eugene conceding that she is in the superior league after all. One by one, the friends line up for their view of Penny's art. As Eugene happily puts it: "Time for a Bruce boost."