In 2006, Oprah and Gayle embarked on the ultimate spa getaway with some deserving O, The Oprah Magazine
contest winners. At the Miraval Resort and Spa in Tucson, Arizona, Gayle—who is afraid of heights—agreed to be hoisted 40 feet in the air for a self-improvement exercise called A Wing and a Prayer. The idea of the exercise was to get over your fears and let yourself drop in the air, all in the name of self-improvement. But there was just one problem: Gayle wouldn't let herself fall.
Watch Gayle try to conquer her fears
Oprah couldn't help but get in some laughs as Gayle struggled with wanting to let go. "It's going to feel like a roller coaster, that's all!" Oprah said. "I hate roller coasters!" Gayle said. Eventually, with Oprah's encouragement, Gayle finally let go—and took off flying!
Look back on all of Oprah and Gayle's great adventures