Planes, Motorcycles, and Turkey Day Car Chaos: Cowboy & Kiki’s Misadventures in Holiday Logistics

Misadventures with Kiki and Cowboy

In this uproarious podcast episode, Cowboy and Kiki dive headfirst into the chaos of planning a blended family Thanksgiving holiday. They riff on the logistics disaster that feels straight out of an '80s comedy like Planes, Trains, and Automobiles, except their version involves planes, motorcycles, cars (lots of cars), and an occasional black hole of miscommunication. Kiki, the pragmatic planner, keeps hitting "cancel" on their annual motorcycle trip reservations, while Cowboy is convinced she’s operating on a different time dimension. Between a surprise work schedule from her son, a daughter flying in from Colorado, and a revolving door of hotel reservations, this holiday has seen more rewrites than a Hollywood blockbuster.

As they recount their "misadventures," Cowboy and Kiki spiral into hilarious tangents. From debating physics (is Kiki the black hole?) to bickering over who’s to blame for last-minute cancellations, their banter is both absurd and relatable. The couple gamely tackles the tangle of kids, transportation, and schedules, with Kiki keeping Cowboy on track while he frets about unplanned expenses. Then, Kiki and Cowboy take us on a wild ride—literally and figuratively—as they navigate a three-car inspection saga that’s straight out of a sitcom. It starts with Kiki's moment of panic over a missed inspection, prompting an impromptu auto shop detour. After roping in her mom for moral support and navigating county inspection myths, Kiki realizes she’s been fretting over the wrong car. Cue a frantic text to her son, who dutifully gets his car inspected, only to uncover a comical cascade of mix-ups involving whose car actually needs attention. Spoiler alert: it’s car #3, but not before the son’s car gets a clean bill of health… with a side of mechanic upselling.

By the time they hit the inspection trifecta, Kiki and Cowboy are philosophical, leaning into the absurdity of closing-time antics at repair shops. Cowboy’s observation about the inspector's evasive “we close in 10 minutes but the wait is 30” math earns a well-deserved eye roll, while Kiki's youngest attempts the nerve-wracking “don’t-drive-into-the-pit” maneuver with a nail-biting audience. With every misstep narrated in sharp, self-deprecating humor, this duo proves that the real adventure is surviving the DMV-inspired madness of holiday logistics. Whether it's misplaced registration fears, overly helpful family, or the unyielding comedy of error-prone planning, this podcast reminds us to laugh—because crying over car inspections is so last season.