15 Things You Didn’t Know About Brad Pitt And Jennifer Aniston’s Relationship

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14. First Date

For their first date, the Benjamin Button actor invited the Friends star over to his place to hang out. They clicked immediately, which led to more low-key dates for the gorgeous couple.

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13. Low Key Romance

Their courtship was really low key. They mostly stayed in, played poker, ate Mexican food and watched TV like a normal couple. “We had so much fun falling in love,” Aniston told Vanity Fair in 2005 after she and Pitt separated. “It was so private; we kept it to ourselves for so long. It was something we were really proud of.”

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12. Getting Married

They announced their engagement at a Sting concert. They joined the band on stage to sing a song about going off to Las Vegas to get married. She then lifted her hand up and all of the concertgoers saw that she was wearing an engagement ring.

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11. Engagement Ring

Pitt designed Aniston’s engagement ring himself. “The story began when casually, Brad Pitt had liked a pair of earrings I had designed after these had won the Diamond International Awards,” the jeweler, Silvia Damiani, told Business Today. “He then requested a special item for his engagement to Jennifer Aniston based on this same model.” In 2001, Pitt sued Damiani International, the company that created the ring, because the ring was supposed to be exclusive and the company had been selling replicas, claiming that they had Pitt and Aniston’s approval.

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10. Video Chatting Before It Was Cool

They spent a lot of time apart during their relationship due to work so, during long absences, they would video chat with each other. This was long before video chatting was popular so, in a way, these two were trendsetters.

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9. Storybook Wedding

Pitt and Aniston were married on July 29, 2000, in Malibu, California, with 200 guests in attendance, 50,000 flowers, four bands, a gospel choir and fireworks. They also wrote their own vows. Pitt promised to “split the difference on the thermostat” and Aniston promised to always make him his “favorite banana milkshake.” To maintain their privacy, they made staffers sign a confidentiality agreement making them liable for a penalty of up to $100,000 if they talked about the wedding and they made an arrangement with the FAA to have an inspector on-site in case the airspace above the property became overcrowded with helicopters.

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8. Completely Honest with Each Other

During their marriage, they tried to be completely honest with one another. It was because of their complete honest with one another that they both discovered that they had respective issues to work through, but they were trying to do it together. “We’ve had this healing process with each other, or deconstructing these ideals of ourselves to get rid of that piece of s–t feeling we carry in ourselves,” she told Vanity Fair. “That kid stuff has given me a career, I’ve channeled it into something positive – being able to make people laugh.”

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7. Conflicts

Brad and Jennifer had their conflicts when they were married, but they did their best to handle it in a mature way. “We do fight,” she told W magazine in 2003 while also mentioned that she has an aversion to conflict. “Well, we have discussions. I am not a fan of fighting when it is screaming. I like accomplishing something. But I don’t trust a couple that says they don’t fight.”

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6. Planning a Pregnancy

Before their separation, Aniston had been expecting to get pregnant. They had agreed that once Friends ended, they would start a family. When they broke up, it was widely believed that she was the one who didn’t want children, but she has contested this.

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5. Warning Sign

During Pitt and Aniston’s marriage, he gave an interview to Vanity Fair where he called their marriage an experiment. He claimed that they had agreed that if it didn’t work out that there would be no hard feelings. This was one of the first red flags.

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4. Clashing Over Architecture

When it came to architecture and interior design, the gorgeous couple often clashed. The L.A. home that they shared was very modern with a lot of hard edges and unforgiving materials, which was Brad’s style. When they broke up, Jennifer told Vanity Fair that she was excited to finally be able to have a comfortable couch again.

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3. Drifted Apart

Friends of Jen’s told Vanity Fair in 2005 that as soon as Brad began working with Angelina Jolie on Mr. and Mrs. Smith, he reportedly checked out of the marriage. This was when Jen was finishing up the last season of Friends, which was a huge loss for her. “That was really painful. It was a family, and I don’t do great with families splitting up,” she said. “It was hard to have such a wonderful constant in your life, a place to go every day, and then all of a sudden it’s not there.” According to her, she tried to reach out to Brad for support, but she didn’t get it. For the final taping of Friends, he didn’t even show up, which shocked those close to Jen.

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2. Attracted to Another Woman

When they split up, Pitt was honest with Aniston about the fact that he was attracted to Angelina Jolie. According to Aniston’s good friend and Friends co-star Courteney Cox, he had tried to fight his attraction to Jolie for a period of time. While there were rumors that Pitt and Jolie had been having a physical affair while filming Mr. and Mrs. Smith, he insisted to Aniston that he hadn’t been intimated with her, which Aniston believed.

Photo by Lionel Hahn/Abaca.

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1. Production Company

Aniston and Pitt formed their own production company, Plan B, with Brad Grey in 2001. Following their divorce, Pitt became the sole owner of the company and Grey went off to become the CEO of Paramount Pictures. Although Aniston had said that she would still produce movies through the company in an interview with Vanity Fair in 2005, she never did. Three of the movies that Plan B has produced – The Departed, 12 Years a Slave and Moonlight – have won the Academy Award for Best Picture.

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Cate

Cate has a B.A. and an M.A. in English Literature and has been the Managing Editor of Fame10 for more than 6 years. Despite having a love for the works of Thomas Hardy, Leo Tolstoy and Lord Byron, she also has an intense fascination with pop culture. When she isn’t writing for Fame10, she’s planning her next big adventure in Southeast Asia.