Brad Pitt and Jennifer Aniston's Relationship from 1994 to Now

While it's been over 15 years since we last saw Jennifer Aniston and Brad Pitt as a couple, their romance is definitely one for the history books. Although the couple was only together for seven years (and married for five!), their A-list relationship did not end with their divorce in 2005. Between their one million dollar wedding, his guest appearance on Friends, and their iconic reunion in 2020, here is everything you need to know about Brad Pitt and Jennifer Aniston's relationship.

• Brad Pitt and Jennifer Aniston first met in 1994, however they didn't begin dating until 1998.
• Brad proposed to Jennifer in 1999 and they wed the following year.
• After five years of marriage, the couple announced their split in early 2005. Brad went on to wed actress Angelina Jolie while Jennifer wed Justin Theroux.
• They both went on to divorce their spouses and have since remained close friends.

1994: A Casual Meeting

Unlike their romance, their first meeting was quite casual. The pair met sometime in 1994 via their managers, who happened to be friends. "He was just this sweet guy from Missouri, you know?” Jen told Rolling Stone in 2001. “A normal guy.” 

1998: The First Date

Their relationship wouldn't turn romantic until their first date four years later. Brad had just broken up with actress Gwyneth Paltrow and Jennifer called it quits with actor Tate Donovan, prompting their managers to set up a date. In 2004, Jen later told Diane Sawyer that the "evening was really easy" and the date "was really fun."

September 12, 1999: Red Carpet Debut

The sparks were ever so present on their first date so the couple dove right into a relationship. They walked the red carpet together for the first time at the 51st Primetime Emmy Awards, confirming relationship rumors in the process.

November 29, 1999: Rocking an Engagement Ring

While attending a Sting concert together on November 29, 1999, the Hollywood stars took the stage to show off Jennifer's new accessory: an engagement ring! The actor reportedly spent $500,000 on the custom bauble, which boasted plenty of diamonds set in a unique circular shape.

July 29, 2000: The Wedding of the Year

The biggest celebrity wedding of 2000 was undoubtedly Brad and Jen's summer nuptials. The couple wed on a bluff overlooking the Pacific Ocean in Malibu in front of 200 guests. Brad wanted the private estate venue to look like a Zen garden so he ordered 50,000 roses, wisteria, tulips, and lotus flowers. A flawless bride, Jen wore a glass-beaded, low-back wedding gown by Lawrence Steele and the newlyweds danced to "The Way You Look Tonight." The over-the-top affair (complete with a 40-person gospel choir, lobster meal, champagne, and a Melissa Etheridge performance) ended with a 13-minute firework show—and cost the couple roughly $1 million.

November 22, 2001: Guest Starring on Friends

The couple acted alongside each other in 2001 when Brad made a guest appearance on Jen's hit sitcom Friends. The episode, called "The One With The Rumor," aired on November 22, 2001, and Brad's character actually hated Rachel Green, who was famously played by his wife.

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

When asked if Brad was the love her life during Jennifer's cover interview for W Magazine in 2003 she responded with, "Is he the love of my life? I think you’re always sort of wondering, ‘Are you the love of my life?’ I mean, I don’t know, I’ve never been someone who says, ‘He’s the love of my life.’ He’s certainly a big love in my life," she told the publication. “And I know that we have something special, especially in all this chaos. In this nutty, brilliant, wonderful, hard business that we have, it’s nice to have somebody who’s anchored and knows you, really knows all of you.”

February 2004: Baby Fever

With the end of Jennifer's time on Friends looming, the actress told The Guardian she was ready to have a baby with her husband of nearly four years. "It's time. It's time. You know, I think you can work with a baby, I think you can work pregnant, I think you can do all of it. So I'm just truly looking forward to slowing down," she said at the time.

May 2004: Mr. and Mrs. Smith

Despite Jen's baby fever three months prior, by May 2004 cheating rumors between Brad and his Mr. and Mrs. Smith costar Angelina Jolie began to swirl. In 2006, Jolie recounted to Vogue how she and Brad began to fall in love on-set of the film, saying, “Because of the film, 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. I think a few months in I realized, ‘God, I can’t wait to get to work.’ … Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair. It took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe. And both knowing that the reality of that was a big thing, something that was going to take a lot of serious consideration.”

January 7, 2005: An Unfortunate Separation

After a nearly five-year marriage and seven-year relationship, Brad and Jennifer announced their split to People on January 24, 2005. The statement read: “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.”

March 25, 2005: Filing the Paperwork

Jennifer filed for divorce from Brad on March 25, 2005. 

September 2005: Jen Addresses the Divorce

While Brad began to flaunt his relationship with actress Angelina Jolie immediately after announcing his separation with Jennifer, the Friends star didn't address the divorce until September 2005. She told Vanity Fair at the time, "Am I lonely? Yes. Am I upset? Yes. Am I confused? Yes. Do I have my days when I’ve thrown a little pity party for myself? Absolutely. But I’m also doing really well. Relationships are two people; everyone is accountable. A lot goes into a relationship coming together, and a lot goes into a relationship falling apart. She’d say, ‘Even if it’s 98 percent the other person’s fault, it’s 2 percent yours, and that’s what we’re going to focus on.’ You can only clean up your side of the street.”

And when the interviewer told Jennifer about the 60-page photo-spread Brad had just posed for with Jolie in W Magazine (entitled "Domestic Bliss"), she replied: "Is it odd timing? Yeah. But it’s not my life. He makes his choices. He can do—whatever. We’re divorced, and you can see why. I can also imagine Brad having absolutely no clue why people would be appalled by it,” she adds. “Brad is not mean-spirited; he would never intentionally try to rub something in my face. In hindsight, I can see him going, ‘Oh—I can see that that was inconsiderate.’ But I know Brad. Brad would say, ‘That’s art!' There’s a sensitivity chip that’s missing."

October 2, 2005: Officially Divorced

Brad and Jennifer's divorce was finalized on October 2, 2005.

September 15, 2011: Brad Comments on the Past

In 2011, Brad made some shady remarks to Parade about his former marriage to Jennifer, telling the publication, "I spent the ‘90s trying to hide out, trying to duck the full celebrity cacophony. I started to get sick of myself sitting on a couch, holding a joint, hiding out. It started feeling pathetic. It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn’t living an interesting life myself. I think that my marriage [to actress Jennifer Aniston] had something to do with it. Trying to pretend the marriage was something that it wasn’t.”

He later, however, issued an apology for his comments in the interview, saying, “It grieves me that this was interpreted this way. Jen is an incredibly giving, loving, and hilarious woman who remains my friend. It is an important relationship I value greatly. The point I was trying to make is not that Jen was dull, but that I was becoming dull to myself—and that, I am responsible for.”

August 10, 2012: Jennifer Is Engaged

On August 10, 2012, Jennifer's boyfriend of one year, actor Justin Theroux, pops the question with a $500,000 engagement ring.

August 23, 2014: Brad Weds Angelina Jolie

After raising six children together, Brad and Jolie finally tied the knot on August 23, 2014. The couple gathered with 22 family members, including their children, Maddox, Pax, Zahara, Shiloh, Vivienne, and Knox, at their French chateau for an intimate wedding ceremony.

August 5, 2015: Jennifer Weds Justin Theroux

A second marriage for Jen, the actress wed fiancé Justin Theroux on August 5, 2015—nearly a year after Brad tied the knot with Jolie.

September 20, 2016: Jolie Divorces Brad

Two years into their marriage, Jolie filed for divorce from Brad, citing irreconcilable differences.

February 11, 2017: The Infamous Text

Newly-single Brad supposedly texted ex-wife Jennifer (who was still married to Theroux at the time) on her 48th birthday in 2017. In addition to sending her birthday wishes, the actor reportedly confided in Jen, with a source saying, "Brad told her he's having a hard time with his split and they exchanged a few texts reminiscing about the past," per Marie Claire.

February 15, 2018: Jen Splits From Theroux

On February 15, 2018, Jennifer announced her split from Theroux after nearly two-and-a-half years of marriage.

February 11, 2019: A Birthday Invitation

Brad scored an invitation to Jennifer's 50th birthday party in 2019, which was held at Los Angeles's Sunset Tower Hotel. Brad's attendance prompted a flurry of media speculation surrounding the couple. In June of that year, Brad responded to a paparazzi cameraman by saying, "Oh my god." Sources close to the couple continued to tell the public the two were just friends.

December 14, 2019: First In, Last Out

After attending her 50th birthday in February, Brad also landed a spot on the guest list to Jennifer's holiday party in 2019. A source told Entertainment Tonight, "[Brad] was among the first to arrive and the second to last guest to leave around 11 p.m."

January 19, 2020: The Photo That Broke the Internet

Early in 2020, Brad referred to Jennifer as a "good friend" but then this happened: The couple reunited on the Screen Actors Guild red carpet and showed off flirtatious body language. After the photographs from the event surfaced (including the one above), fans everywhere hoped the pair would get back together.

September 17, 2020: Flirty Characters

Brad and Jen reunited again in September 2020 for a charity table read of the 1982 movie Fast Times at Ridgemont High. Starring alongside other actors—Morgan Freeman, Matthew McConaughey, and Julia Roberts—Jennifer and Brad played characters, Linda and Brad, respectively. The couple exchanged flirty dialogue, with Jen as Linda saying, "Hi Brad, you know how cute I always thought you were? I think you're so sexy, will you come to me?"

June 2021: Jen Sets the Record Straight

Almost a year after their flirty table read, Jennifer set the record straight about where her relationship with Brad stands. During an appearance on The Howard Stern Show, Stern asked Jen if the former couple’s virtual reunion was awkward for the actress.

"No!" Jennifer told the host. "It was absolutely fun. You know, Brad and I are buddies. Like, we're friends and we speak."

"There's no oddness at all," she went on, "except for everyone that probably watched it and was wanting there to be." And there you have it: Despite their shared history, Brad and Jen are still “buddies” to this day.

A week later, Jennifer spoke to People about her thoughts on remarrying.

"I'm interested in finding a fantastic partner and just living an enjoyable life and having fun with one another," she said. "That's all we should hope for. It doesn't have to be etched in stone in legal documents."

She continued to remark on her disinterest in online dating, explaining: "I'm going to just stick to the normal ways of dating. Having someone ask you out. That's the way I would prefer it."