9. Matthew Perry’s Real Life
On Friends, Chandler struggled with the ladies. Matthew Perry, who played Chandler, played him as a charming but awkward guy. He’s not very good at picking up women, despite being a good looking dude. In a classic case of life imitating art, Matthew Perry is about the same in his real life. “One of the producers came up and asked me one Monday how a date had gone over the weekend,” he told People Magazine in 1995. “I said, ‘It went great. We went out for dinner, then for a nice walk on Melrose and back to her place, where we shared a nice kiss good night. And I’m pretty confident that I’m going to die alone.’”