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!
Gayle's date with bachelor number one, Bill, a single father of two young sons, was at the Four Seasons in New York City. When she arrived at the hotel, Gayle's nerves almost got the best of her. "I said, 'Is it too late just to turn around and go back to Connecticut?'" Gayle said "I can't believe that I'm actually nervous about this. This is so silly!" Turns out, Bill was a nice guy, and Gayle even agreed to a second date.