202: The “Maybe Don’t Do That” Episode

What happens when criminals make every possible wrong decision… and then double down? In this episode of The Shallow End, we dive headfirst into a series of real-life stories that prove you don’t need a mastermind to commit a crime—sometimes all you need is spectacularly bad judgment. First, meet Darren Kimpton—a burglar having what can only be described as an aggressively terrible day. After botching one break-in and leaving behind a literal trail of blood (yes, DNA included), he decides the logical next step is… to try again. What follows is less of a crime and more of a live-action surrender. Then, things shift from clumsy crime to courtroom chaos. A woman named Kimberly Carroll attempts to attend a virtual court hearing via Zoom—while driving. What unfolds is a painfully awkward, wildly viral moment involving a skeptical judge, a very obvious lie, and one of the most expensive car rides imaginable. Plus, listener stories that will make you question how anyone boards the wrong plane—and doesn’t realize it until takeoff. This episode is packed with: Dumb criminal fails (the kind that practically solve themselves) Viral courtroom moments you have to hear to believe Absurd real-life stories that feel scripted… but aren’t The kind of humor that makes you grateful you’re not that person If you love true crime with a comedic twist, unbelievable real-life mishaps, and stories where everything goes wrong in the most entertaining way possible—welcome to The Shallow End. Learn more about your ad choices. Visit megaphone.fm/adchoices