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.