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Jennifer Aniston, 52, and Brad Pitt, 57, are one of Hollywood’s most iconic couples. The pair’s relationship has been quite a rollercoaster through the years, from marriage to divorce, nemeses to pals, these two have been through it all. Though after all these years, Jen has nothing but positive attitude towards Brad and the FRIENDS actor said good things about her ex-husband in the recent interview. The former it-couple have been broken up for 15 years, and seem to be healing as they have moved on with their lives and share positive vibes.

After being set-up by their respective managers for a typical Hollywood style date, Jen and Brad had their first classic evening in 1998. In an interview with Rolling Stone, Jen said their managers were friends. “[Pitt] was just this sweet guy from Missouri, you know? A normal guy,” she told the outlet. During a 2004 interview with Diane Sawyer on ABC’s Primetime, Jen said that she knew she and Brad were meant to be on that first date, explaining, “It was weird … That was a really easy evening. It was really fun.” They eventually made things official when they stepped out on the red carpet together at the Emmy Awards in 1999, and got engaged just months later! They crashed a Sting concert, and appeared on stage in New York City to flash the Friends star’s massive diamond ring (well, we didn’t have Instagram back then!). The couple said their ‘I do’s on July 29 in the year 2000, in front of 200 guests, with a lot of lavish trimmings including 50,000 flowers, four bands, a gospel choir, and fireworks to end the night. Jennifer told Rolling Stone in 2001, “I had those typical jitters the day before my wedding, but the day of, I was just excited in a good way.” The wedding was one of the greatest news of that era.

Brad also had a cameo in the famous sitcom, F.R.I.E.N.D.S, where Jen played Rachel Green. He portrayed Rachel Green’s old classmate, Will in the season eight episode, where it was revealed that while back in high school Ross and Will had opened ‘I hate Rachel Green’ club and was one of the hilarious and most memorable moments from the series. In the recent 2021 Friends reunion, Jen revealed he was one of her favourite guest stars. The actress referred to her ex-husband as “Mr. Pitt” when bringing him up along with other talented actors such as Sean Penn and Ben Stiller.

The couple announced their split in January 2005, and many rumors started surfacing the split. When the couple, in a joint statement, announced their divorce in 2005, said: “We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”

Reportedly, while shooting for Mr. and Mrs. Smith, Brad was casted opposite Angelia Jolie. Pitt fell for Jolie on the set of the movie and to fans surprise, they were spotted together on a vacation just a little after Pitt and Aniston called it quits. This led to rumors circulating about Brad cheating on Jen. The couple tied their knot in September 2014 and divorced in 2016. Meanwhile, Jennifer tied the knot with Justin Theroux in August 2015 but the couple announced their separation in February, 2018.

Almost 20 years after the pair wed, they reunited at Jen’s 50th birthday party at the Sunset Tower Hotel in Los Angeles. The following year they were seen chatting it up behind the scenes at the 2020 SAG Awards on January 19, 2020. “Brad was there at the first backstage finishing photos and saw Jen in the corner of his eye when she came to the back,” a Hollywood Life source dished EXCLUSIVELY on January 22. “He repeatedly called for her to come over and kept saying, ‘Aniston, Aniston.’ He never called her Jen. She heard him but didn’t respond and almost went to the other room to avoid the meet-up.” The brief encounter quickly went viral, and did little to quell fans’ hope that the pair would one day reunite romantically. Now, the pair is sharing a good and healthy friendship and is happy without any hard feelings.