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Julia Roberts

Perry and Roberts began dating in 1995, around the time when Roberts prepared to guest star on "Friends". But Perry's insecurities led him to break up with her.

"Dating Julia Roberts had been too much for me," he wrote. "I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."

Image Source: Getty / Getty Images