Tate Donovan found it difficult to shoot Friends with Aniston(Photo Credit – YouTube)

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During Jennifer Aniston’s run as Rachel Green on the hit sitcom Friends, she had several of her real partners make guest appearances on the show.

The most notable and memorable was Brad Pitt, who appeared as Will Colbert, a character who hated Rachel in high school. The guest spot is particularly unforgettable because many fans thought Pitt would play a romantic interest, instead, he ended up playing a different character. However, not all of Aniston’s guest-starring roles with partners went smoothly as there was one ex who had a challenging time during his cameo on Friends.

In 1995, Aniston began dating Tate Donovan. While the two lasted in a two-year relationship, they ended up playing each other’s love interest on Friends after they had broken up. Donovan played Rachel’s boyfriend Joshua for six episodes of Friends, as the actor once shared with the US Weekly how uncomfortable it got for him.

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He shared, “I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time. And so that was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up. That was just tough.”