Getty One of Andy Cohen's past flings is looking back at their romance! If you didn't know, the 57-year-old Watch What Happens Live host had a fling years ago with Broadway star Sydney James Harcourt. While appearing on the Tuesday (April 28) episode of the Dads and Daddies podcast, Sydney, 50, shared some intimate details of his fling with Andy. After stressing that their fling wasn't just a one night stand, Sydney said that he and Andy initially met on Craigslist and saw each other on and off for "at least a year and a half.