Across its ten seasons, Friends became iconic not just for its humor but for its star-studded guest appearances. From Bruce Willis to Jon Favreau, the show often brought in big names to shake up the love lives of its six main characters.
One of the most memorable came in Season 4, when Tate Donovan played Joshua, Rachel Green’s charming Bloomingdale’s client. The role was especially interesting because Donovan had just broken up with Jennifer Aniston in real life before filming. Despite the emotional timing, he delivered a great performance — though knowing the real story behind it makes those scenes even more bittersweet.
Tate Donovan Played Joshua in Friends
He Appeared in Five Episodes
In 1998, Tate Donovan appeared in a five-episode arc as Joshua Burgin, one of Rachel Green’s clients at Bloomingdale’s. Recently divorced and wealthy, Joshua quickly caught Rachel’s attention — but her attempts to win him over were a series of hilarious misfires. From botching a basketball game invite to accidentally scaring him off in a wedding dress, Rachel’s pursuit of Joshua was a mix of charm and chaos.
Despite her best efforts, Joshua ultimately turned Rachel down, explaining that he wasn’t ready for a new relationship after his divorce. Their short-lived romance ended awkwardly but memorably, making Joshua one of Friends’ most talked-about guest love interests.
Donovan Was Cast on Friends While Breaking Up With Jennifer Aniston
He Described the Experience as “Tough”
Tate Donovan and Jennifer Aniston had been together for two years before their breakup — which happened right as Donovan joined Friends to play Rachel’s love interest, Joshua. Ironically, he had been a regular at the show’s live tapings, often attending to support Aniston. Donovan even pitched the idea of Rachel falling for a man who doesn’t like her back — a concept that later became the very storyline he starred in.
Filming those episodes while navigating a real-life split made the experience especially painful. Donovan admitted it was “tough,” comparing it to “going to class in high school after breaking up with the girl you sat next to.” Despite the awkwardness, the cast was supportive — especially Matthew Perry, who reached out to him during the breakup.
“Matt was such a champion of mine,” Donovan said. “He was the only one who called me when Jen and I broke up… It meant so much because I was really heartbroken.” He added that Perry’s kindness stayed with him for years, calling it “a tragedy” that someone so generous and funny struggled so deeply in his own life.
Rewatching Friends Gave Tate Donovan a Confidence Boost
He Definitely Liked What He Saw
Years after his Friends appearance, Tate Donovan stumbled upon one of his episodes while flipping channels at a hotel. Now known for roles in The O.C. and Argo, Donovan couldn’t help but laugh at what he saw — and, admittedly, at how good he looked back then. Reflecting on the moment, he joked, “Wow, I was really handsome at one point in my life.”
