Oprah's Best Friend Gayle Goes on Blind Dates
Dating is difficult for many people, but Oprah's best friend Gayle said it was especially hard for her as a divorced mother of two. Gayle voiced her relationship woes on a show called Dating Over 35. After the show, Gayle was bombarded with mail from men who wanted to take her out on the town. So, in 2003, she stepped out of her comfort zone and went on four blind dates—with Oprah Show cameras filming every moment!