The two first met back in 1994 and, in an interesting twist, were set up by their agents. Depending on the power given to them, agents can act as guardians of both a celebrity’s career and also of personal matters that may be in their client’s best interest.
In this case, however, the two agents were friends and thought that the stars would hit it off. Yet perhaps, given that both Brad and Jen were rising stars, the agents may have also thought it’d be a great publicity move. And, at least at the beginning, the agents were right.
Tate Donavan — a Sad Day on Set
Obviously, Jennifer Aniston and Tate Donavan’s relationship would have become very, very serious if the two were engaged. Even though they broke off the engagement and the relationship, the two professionals continued their work on “Friends'' together, but that didn’t mean it was an easy or enjoyable time.
Tate admitted that he felt like he was “dying inside” while working on the set with his ex. It was so tortuous that when they finally wrapped the last scene, Donavan went back to his trailer and cried. Sounds a bit traumatic. Now that’s a bad day at work!
Perhaps one of the most iconic celebrity couples, Jen and Brad Pitt were Hollywood royalty. And, of all her romances, any fans consider this her greatest, although Pitt didn’t end up being the man she deserved.
Jenn and Brad began dating in 1998 and were at the altar in the year 2000. They were married for five years until the marriage became rocky due to rumors of Brad’s relationship with his “Mr. & Mrs. Smith” co-star Angelina Jolie. The two decided to split in 2005. Surprisingly, they remained on congenial terms despite the supposed infidelity and their highly publicized divorce.
Brad Pitt — a Whirlwind Romance
The celebrities officially began dating in 1998. Their pairing truly appeared to be a match made in Hollywood heaven. Although they tried to keep their relationship private for a time, they decided not to hide it anymore when they appeared on the red carpet at the Emmys in 1999.
Just later that year, the two were so head-over-heels for each other that, while attending a Sting concert, they took to the stage to announce that they were engaged! Jen made sure to give the audience a look at her stunning engagement ring. How’s that for an interruption?
Brad Pitt — The Hollywood Fairytale
Jen and Brad headed to the altar the following year in Malibu with paparazzi lurking outside the venue. The wedding was notable because the reception ended with a stunning fireworks display. After the wedding, the honeymoon phase seemed to last, with the newlyweds making more red-carpet appearances and with Jen sharing her long-term relationship advice with reporters.
While married, Brad even made a notable appearance on “Friends” playing a character who hated Rachel. Certainly an ironic casting. And sadly, as it seems most “Hollywood fairytale” romances turn out, their relationship was headed for a dead end.