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Jennifer Aniston and Her Men

Don't mix business with pleasure! In the mid-'90s, Jen dated Tate Donovan, who guested on Friends as Rachel's crush, Joshua. The two split in reel and real life. "She likes top-notch hotels and luxury, and I like bed-and-breakfasts and riding my bike," Tate has said of their incompatibility. "That's the most shallow version of it, but it's indicative of our personalities."