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Tate Donovan

The couple began dating in 1995 and had already been together for a while before he played her love interest Joshua on "Friends." However, Donovan said "didn't know who" Aniston was before dating her and had "never seen 'Friends,'" according to E! News. There were rumours that Aniston and Donovan got engaged in 1997, but Aniston told People (via E! News), "There's nothing to report. You have to take more time to get to know someone." They eventually broke up in 1998.

Image Source: Getty / KMazur