Matthew Perry Admits His Past Smitten Feelings For Jennifer Aniston Weren't Mutual

Matthew Perry may be a Hollywood star, but that doesn't mean he had a way with the ladies. Well, not before landing the role of Chandler Bing on "Friends," anyway. In his candid new memoir, "Friends, Lovers, and the Big Terrible Thing," Perry opens up about his childhood and longtime struggle with addiction. He also confesses that he had a massive crush on one of his co-stars that began even before Central Perk served its first cup of joe.

Sadly, it was an unrequited love that could've made for some pretty awkward filming. But then, some of the "Friends" cast did date off-set, so they were used to mixing business with pleasure gone wrong. "Friends" ran for 10 seasons before ending in 2004. Per IMDb, the sitcom detailed the ups, downs, and all-arounds of "the personal and professional lives of six twenty to thirty-something-year-old friends living in Manhattan." The finale left fans heartbroken and still pondering how a waitress and a chef could afford such a sweet pad in a prime West Village location. (According to CNBC, Monica Gellar inherited the rent-controlled apartment from her gran, so it only cost $200 a month).

On "Friends," Chandler's madly in love with Monica and not just for rent control purposes. People notes that the two end up married and welcoming two children together. But, in real life, Perry had set his eyes on a different co-star prize: Rachel Green. However, Perry admits his smitten feelings for Jennifer Aniston weren't mutual.

Before they found fame, the cast of "Friends" experienced the hustle and grind all aspiring actors endure. Jennifer Aniston strared in a slew of failures before scoring the role of Rachel Green. "I was such a loser," she told People. Meanwhile, Matthew Perry's life before "Friends" involved a lot of "winning." The Canadian was an up-and-coming tennis player with a wicked serve and a killer backhand.

"I had this incredible drive on the tennis court, and that translated into acting," he told The New York Times about swapping the court for the camera. Perry's "incredible drive" may have aided his TV career, but it didn't help his love life. In his memoir (via Page Six), the star admits to having met Aniston before their "Friends" days and falling hard. He once called her to share the news that he'd landed two acting gigs.

However, Aniston was less than impressed and saw it as a guise to try and hit on her again. "It was clear that this made her think I liked her too much," Perry admits. He continued to ask her out, though, even during the filming of "Friends," but to no avail. Thankfully, by the time Aniston met her future husband-turned-ex, Brad Pitt, Perry had gotten over her. Perry began dating Julia Roberts, who had been a guest star on "Friends." In the episode, they pashed, then she dashed, leaving Chandler wearing a thong in a bathroom stall. Oh, well...