Columbus Short
The 'Scandal' star claimed that Britney had thrown him an elaborate 21st birthday party and rumors swirled that the two were dating but he later wrote it off as a one-time fling. He wrote in his autobiography: "We ended up being intimate that one time. I never slept with her again after that, though. This was a dangerous sexual alliance for every reason under sun, and I think that the worst part of it was that I was making the rumors an actual reality."