Jennifer Aniston & Brad Pitt – Relationship Timeline, Ups & Downs & Hopes

Even though it has been more than 15 years since we last saw Jennifer Aniston and Brad Pitt together, their romance is undoubtedly one to remember. Even though they were only married for five years and seven years, respectively, the couple’s A-list romance continued until their divorce in 2005. Here is all you need to know about Brad Pitt and Jennifer Aniston’s relationship, from their $1 million wedding to his Friends appearance and their historic reunion in 2020.

Despite first meeting in 1994, Brad Pitt and Jennifer Aniston didn’t start dating until that year.
In 1999, Brad got down on one knee and asked Jennifer to marry him.
Early in 2005, the pair announced their separation after five years of marriage. Jennifer then married Justin Theroux, while Brad later wed actress Angelina Jolie.
After divorcing their wives, they both continued to be close friends.

1994: A Casual Meeting

In contrast to their relationship, their first encounter was very informal. In 1994, the two came into contact through their managers—who also happened to be friends. He was simply this nice Missourian guy, you know? In 2001, Jen spoke with Rolling Stone. “A regular person.”

1998: The First Date

The two of them wouldn’t start dating until four years after they initially met. Their managers arranged a date after Brad and Jennifer called it quits with Tate Donovan and Gwyneth Paltrow, respectively. The “evening was pretty simple” and the “date was incredibly fun,” Jen subsequently said to Diane Sawyer in 2004.

September 12, 1999: Red Carpet Debut

On their first date, there were obvious sparks, and they immediately started dating. At the 51st Primetime Emmy Awards, they had their first red carpet walk together, putting relationship rumours to rest.

November 29, 1999: Rocking an Engagement Ring

On November 29, 1999, while seeing a Sting concert together, the Hollywood A-listers climbed the stage to display Jennifer’s newest accessory: an engagement ring! According to reports, the actor paid $500,000 on the handcrafted jewellery piece, which featured many diamonds placed in an unusual circular shape.

July 29, 2000: The Wedding of the Year

Brad and Jen’s summer wedding was arguably the largest celebrity wedding of 2000. In front of 200 guests, the couple exchanged vows atop a hillside in Malibu that overlooked the Pacific Ocean. Brad bought 50,000 roses, wisteria, tulips, and lotus flowers to make the private estate setting appear like a Zen garden. Jen was a picture-perfect bride in a low-back, glass-beaded Lawrence Steele wedding gown as the newlyweds danced to “The Way You Look Tonight.” The extravagant celebration, which cost the couple almost $1 million, included a 40-person gospel choir, a lobster dinner, champagne, a Melissa Etheridge performance, and a 13-minute fireworks display.

November 22, 2001: Guest Starring on Friends

In 2001, the pair appeared on-screen together when Brad made a cameo on Jen’s popular comedy Friends. The popularly played Rachel Green, who was portrayed by Brad’s wife, was truly disliked by his character in the episode, “The One With The Rumor,” which aired on November 22, 2001.

February 1, 2003: Is He the Love of Her Life?

During her 2003 cover interview with W Magazine, Jennifer was questioned if Brad was her true love. She replied, “Is he the love of my life? I believe you frequently ponder the question, “Are you the love of my life?” I mean, I dunno; I’ve never been the type of person to declare, “He’s the love of my life.” He’s definitely a significant love in my life, she told the media. “And I am confident that despite the craziness, we have something great. It’s fantastic to have someone that is grounded and truly knows all of you in this crazy, creative, wonderful, challenging profession that we are in.

February 2004: Baby Fever

The actress Jennifer said she was prepared to have a child with her husband of almost four years as the end of her stint on Friends drew near. It’s now. It’s now. You know, I think you can work when pregnant and with a baby. I think you can handle anything. Then, she remarked, “I’m really really looking forward to slowing down.

May 2004: Mr. and Mrs. Smith

Despite Jen’s baby fever three months earlier, by May 2004 there were suspicions of infidelity between Brad and his co-star in Mr. and Mrs. Smith, Angelina Jolie. When Jolie and Brad first started dating, it was on the set of the movie, she recalled to Vogue in 2006. She added, “Because of the movie, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened. A few months in, I believe I came to the realisation, “God, I can’t wait to get to work.” Any task we had to complete together brought us great joy and required a lot of genuine teamwork. We just started to act like a couple. Really, I don’t think we understood that it might mean more than we’d initially allowed ourselves to believe until the very end of the shoot. And both of them were aware that reality was a significant issue that required careful study.

January 7, 2005: An Unfortunate Separation

Brad and Jennifer split up on January 24, 2005, after a relationship of seven years and a marriage of almost five. We would like to announce that after seven years of marriage, we have made the decision to formally divorce. We would want to clarify for those who are interested in this sort of thing that none of the rumours reported by the tabloid media are the cause of our split. This choice is the result of careful thought and deliberation. We continue to be devoted, thoughtful friends who greatly adore and respect one another. We kindly request your consideration and goodwill throughout the upcoming months.

March 25, 2005: Filing the Paperwork

Jennifer filed the necessary paperwork to divorce Brad.

September 2005: Jen Addresses the Divorce

Jennifer Aniston grinning while pointing a camera
The Friends actor didn’t discuss the divorce until September 2005, whereas Brad started to publicise his romance with actress Angelina Jolie as soon as he announced his separation from Jennifer. “Am I lonely? ” she asked Vanity Fair at the time. Yes. Am I angry? Yes. Am I unclear? Yes. Do I occasionally indulge in a small self-pity party? Absolutely. However, I’m also doing really well. In a relationship, there are two parties, and each is responsible. A lot goes into building a relationship, and a lot goes into it breaking down. Even if it’s 98 percent the responsibility of the other person, she would assert, “It’s only 2 percent your fault, and that’s what we’re going to concentrate on.” Only your side of the street can be cleaned.

And Jennifer said, “Is it odd timing? ” when the interviewer mentioned the 60-page photo shoot Brad had just appeared for with Jolie in W Magazine, titled “Domestic Bliss.” Yeah. However, that isn’t my life. He decides what to do. Anything is possible for him. You can see why we got divorced. I can also see Brad not understanding at all why people would find that repulsive,” she continues. Brad is not a spiteful person; he would never try to deliberately rub something in my face. In retrospect, I can imagine him thinking, “Oh—I can see that it was unkind.” But I do know Brad. In Brad’s words, “That’s art!” There is a missing sensitivity chip.

October 2, 2005: Officially Divorced

October 2, 2005, Brad and Jennifer’s divorce became official.

September 15, 2011: Brad Comments on the Past

Brad made some questionable comments to Parade in 2011 regarding his divorce with Jennifer. He said, “I spent the ’90s trying to hide away, trying to escape the whole superstar noise. I grew tired of hiding out, smoking a joint, and sitting on a couch. It began to seem pitiful. It became very evident to me that while I wasn’t living an exciting life myself, I was determined to discover a movie about an intriguing life. My marriage to Jennifer Aniston, an actress, may have played a role. Making an effort to pass off the marriage as something it wasn’t.

He later apologised for his remarks in the interview, adding, “It grieves me that this was perceived in this way. Jen is still my friend and she is an extraordinarily caring, loving, and funny woman. I place a lot of emphasis on this significant relationship. The argument I was making was not that Jen was uninteresting, but rather that I was, and that I was to blame.

August 10, 2012: Jennifer Is Engaged

Actor Justin Theroux, Jennifer’s longtime boyfriend, proposes to her on August 10, 2012, wearing a $500,000 engagement ring.

August 23, 2014: Brad Weds Angelina Jolie

On August 23, 2014, Brad and Angelina Jolie wed after co-parenting six children. The couple held a small wedding ceremony in their French castle with 22 members of their family present, including their children Maddox, Pax, Zahara, Shiloh, Vivienne, and Knox.

August 5, 2015: Jennifer Weds Justin Theroux

Almost a year after Brad wed Angelina Jolie, Jen married Justin Theroux on August 5, 2015, marking her second marriage.

September 20, 2016: Jolie Divorces Brad

Jolie and Brad divorced after two years of marriage due to their irreconcilable disagreements.

February 11, 2017: The Infamous Text

Newly-single On Jennifer’s 48th birthday in 2017, Brad allegedly contacted her (who was still wed to Theroux at the time). The actor reportedly texted Jen to wish her a happy birthday as well as to share some personal information. According to a source, “Brad informed her he’s having a hard time with his split and they exchanged a few texts reminiscing about the past.”

February 15, 2018: Jen Splits From Theroux

After over 2.5 years of marriage, Jennifer made the announcement that she and Theroux were divorcing on February 15, 2018.

February 11, 2019: A Birthday Invitation

Brad received an invitation to Jennifer’s 50th birthday celebration in 2019 at the Sunset Tower Hotel in Los Angeles. Following Brad’s participation, there was a rush of couple-related media conjecture. Brad said, “Oh my gosh,” in response to a paparazzi photographer in June of that year. The public was repeatedly told by those close to the couple that they were merely pals.

December 14, 2019: First In, Last Out

Brad was invited to Jennifer’s holiday party in 2019 after attending her 50th birthday celebration in February. “[Brad] was among the first to arrive and the second-to-last guest to leave around 11 p.m.,” a source told Entertainment Tonight.

January 19, 2020: The Photo That Broke the Internet

Brad initially referred to Jennifer as a “good friend” in the beginning of 2020, but then this occurred: The couple reunited on the red carpet of the Screen Actors Guild and displayed flirty body language. All over the world, fans hoped the couple would reconcile after the event’s photos (such as the one shown above) surfaced.

September 17, 2020: Flirty Characters

In September 2020, Brad and Jen got back together for a charity table read of the 1982 film Fast Times at Ridgemont High. Jennifer and Brad co-starred with Julia Roberts, Morgan Freeman, and Matthew McConaughey as the characters Linda and Brad, respectively. Jen, playing Linda, said to Brad, “Hi Brad, you know how cute I always thought you were? They engaged in flirtatious conversation. I believe you’re very sexy, will you come to me?”

June 2021: Jen Sets the Record Straight

Almost a year after their steamy table read, Jennifer laid the record straight about where her relationship with Brad is. During an interview on The Howard Stern Show, Stern questioned Jen if the former couple’s virtual reunion was awkward for the actress.

“No!” Informed the host, Jennifer. “It was really enjoyable. I’m friends with Brad, as you may know. Like, we speak and are pals.

She continued, “Except for everyone who undoubtedly saw it and wanted there to be, there’s no oddness at all. And there you have it: Brad and Jen are still “buddies” today despite having a common past.

Jennifer talked to People a week later about her ideas towards remarriage.

She remarked, “I’m interested in finding a great spouse and simply living a fun life and having fun with each other.” “That’s the best we can hope for. Legal documents don’t have to spell it out in black and white.

She went on to say that she was not interested in internet dating and said, “I’m just going to stick to the usual ways of dating. getting a date request. That’s how I would like it to be.

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Being a binge-watcher himself, finding Content to write about comes naturally to Divesh. From Anime to Trending Netflix Series and Celebrity News, he covers every detail and always find the right sources for his research.

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