From Julia Roberts To Lizzy Caplan

After having his first drink at age 14, Matthew Perry's lifelong relationship with alcohol was in its infancy when the teenager's early sexual experimentation led him to conclude he was impotent — not realizing it was all that drinking that led to his inability to perform. It wasn't until he was 18, and began dating Tricia Fisher (half-sister of Carrie Fisher) that he made the connection. 

As he wrote in his 2022 memoir, "Friends, Lovers, and the Big Terrible Thing," he initially told Fisher he was planning to remain a virgin until his wedding night — a cover for his presumed impotence. "My firmness, at least in my conviction to wait, lasted two months," Perry wrote (via PopSugar). Perry's plan lasted until Fisher got him alone one night and took things to the next level. Perry felt obliged to share his shameful secret with her, but she was undeterred, promising him that everything would work just fine. She was right. "Sure enough, sheer glory for two whole minutes," he wrote (via Yahoo! Entertainment). After Fisher helped him realize there really was no problem, he joked that he paid her back by "sleeping with almost every woman in Southern California."

They broke up, but reconnected and resumed their romance several years later, while Perry was starring on "Friends." Their second stab at love, however, ended much like the first. "She didn't abandon me," he wrote, "but old fears crept up, and I ended the relationship."

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