This heartwarming story of a chance encounter with Oprah Winfrey at a high-end restaurant in Wellesley, MA showcases not only the author’s awe but also Oprah’s kindness and graciousness as a guest. The author, a waiter tasked with managing Oprah’s reservation, is greeted warmly by Oprah and asked for menu recommendations, to which he responds with as much grace as he can muster. Meanwhile, Oprah’s bodyguard, Willingham, keeps a watchful eye on everything, including leaving a generous 100% tip on their tab. This tale is a testament to the power of kindness and the humanity of celebrities, and serves as a reminder that anyone can make a difference in someone else’s day if they just take a moment to be considerate.