Even though Jennifer Aniston's love life has been a rollercoaster, full of public highs and lows and messy courtships, she started off her history of love affairs with something really pure. As she told Rolling Stone in 1999, her "first real, mature relationship" didn't happen until she moved to California. She revealed that his name was Daniel McDonald, an actor nominated for a Tony for "Steel Pier" at the time. He appeared in several movies from 1984 to 1998 and appeared on TV episodes of "Law & Order," "Murder, She Wrote," and "Sex and the City."

"When we broke up, he moved to New York and started doing great," Aniston told Rolling Stone. "Just before 'Friends,' we broke up." She said that he was "just wonderful" and a "dear friend" when it came to her newfound fame. Over a decade later, Aniston told the New York Times in 2015 how fondly she looks back on McDonald. "He was my first love — five years we were together," she said. "He would have been the one. But I was 25, and I was stupid. He must have sent me Justin [Theroux] to make up for it all." This is referring to the fact that McDonald died of a brain tumor in 2007 at the age of 46, suggesting that maybe he was a guardian angel who came down to send her Theroux, her fiance at the time. 

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