Swing & Miss! Matthew Perry Once Awkwardly Told Jennifer Aniston 'We Can't Just Be Friends' After She Rejected Him

Matthew Perry opened up about his crush on Jennifer Aniston and how he handled rejection in the pages of his memoir, Friends, Lovers And The Big Terrible Thing, which is set to hit shelves on Tuesday, November 1.

The sitcom star admitted he developed feelings for Aniston before they were even costars — and once tried to impress her by calling her on the phone and bragging about booking several acting gigs.

Despite noting that "it was clear" the Just Go With It star immediately felt he "liked her too much, or in the wrong kind of way," he still asked her out on a date.

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Although Aniston politely said no to his offer, she did ask if they could still be friends, to which Perry awkwardly exclaimed, "[We] can't be friends!"

Perry confessed that he still had a lingering crush on Aniston when they both landed roles on Friends in 1994, but thankfully, they were "able to sail right past the past and focus on the fact that we had both gotten the best job Hollywood had to offer."

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And while he overanalyzed their interactions for some time, hoping for hints at a change of heart, the actress showed a "deafening lack of interest" in a romantic relationship with him.

The 17 Again star may not have hit it out of the park with Aniston, but he did share the story of how he caught Julia Roberts' eye — only to break it off after struggling with not feeling good enough for the Pretty Woman actress.

"I let her in, both figuratively and literally, and a relationship began," Perry said in another excerpt of the upcoming book. "We would already be a couple by the time we started filming the Friends Super Bowl episode."

However, the actor explained his whirlwind romance with Roberts was "too much" for him, as he struggled with his own inner demons.

"I could never be enough; I was broken, bent, unlovable," he added. "So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."