"I was too fond of her...": When Matthew Perry asked out FRIENDS co-star Jennifer Aniston, but she turned him down

Matthew Perry, renowned for his unforgettable portrayal of Chandler Bing in the much-loved sitcom FRIENDS, has recently opened up about a heartfelt revelation involving his co-star Jennifer Aniston. Perry revealed that well before their on-screen camaraderie on FRIENDS, he had mustered up the courage to express his romantic interest to Aniston. Unfortunately, his advances were graciously declined, initially creating an awkward dynamic between them. However, over time, that initial discomfort transformed into a deep and enduring friendship.

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Matthew Perry revealed having a crush on Jennifer Aniston

Perry in his book, retrieved from Entertainment Weekly, candidly admitted that he had a major crush on Aniston. He couldn't help but be drawn to her charisma and charm of the actress and shared, "I was immediately taken by her (how could I not be?) and liked her, and I got the sense she was intrigued, too." 

Perry even shared that at that time he received two jobs together and shared this good news with Jennifer Aniston, only to realize later that it was a “bad idea”. “Back then I got two jobs in one day — one was Haywire, an America's Funniest Home Videos-type show, and the other was a sitcom. So I called Jennifer and I said, 'You're the first person I wanted to tell this to!'” However, Perry confessed that he might have come on too strong, and this may have led Jennifer to have a bad impression of him. "Looking back, it was clear that this made her think I liked her too much or in the wrong kind of way," Perry shared. 

Despite this initial miscommunication, Perry took a leap of faith and asked Jennifer out on a date, a request she graciously declined. Reflecting on the situation, Perry noted, "I only compounded the error by then asking her out. She declined (which made it very difficult to actually go out with her), but said that she’d love to be friends with me, and I compounded the compound by blurting, 'We can’t be friends!'"

Matthew Perry on the awkwardness of working alongside her one-sided crush in Friends

The confession of Perry definitely made it a bit difficult for both the stars to work together on the sets of FRIENDS. This twist of fate led to moments of awkwardness, particularly for Perry, who was still harboring a crush on his co-star. In the early days of the show's production, Perry admitted that interacting with Jennifer became challenging because of his feelings. Perry revealed, “Fairly early in the making of Friends I realized that I was still crushing badly on Jennifer Aniston. Our hellos and goodbyes became awkward. And then I'd ask myself, How long can I look at her? Is three seconds too long?"

Time, as they say, heals all wounds. Matthew Perry's lingering crush on Jennifer Aniston slowly began to fade as the immense popularity of the 90s series took center stage. Nonetheless, both the stars overcame the past and built upon their present strong friendship by working along in the iconic sitcom, Friends. 

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