Inside Brad Pitt and Jennifer Aniston’s Relationship — a Tale about one of Hollywood’s Love Stories That Didn’t Make It

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Youtube/Nicki Swift

For five years, Hollywood veterans Brad Pitt and Jennifer Aniston were the roleplayers in one of the best off-screen romance in Hollywood.

Brad Pitt and Jenifer Aniston’s love story began and subsequently ended over two decades ago. Yet, it still passes for one of the most epic love tales to play out in the real world.

Although it lasted barely five years, that was all the time it took to make the one-time couple pair a fan-favorite. Their divorce in 2005 swept the world by surprise, leaving most people worried about the fate of the love birds.

Image: YouTube/ Clevver News

Almost twenty years and several spouses later, many are still rooting for a Brad-Jennifer replay, holding on to the tiniest hope of the pair reuniting. While it lasted, though, their whirlwind romance was considered the rare Hollywood success.

BRAD PITT AND JENNIFER ANISTON’S FIRST MEETING

Pitt and Aniston’s first meeting happened in 1998. Their respective agents set them up on a date, and they connected instantly. In a 2004 interview, Aniston admitted that the date was a fun one, and left them knowing they had each found something special.

However, prior to this first date, their paths crossed in 1994 since their managers were friends. Although there were no formal introductions, Pitt proved himself to be the “sweet guy.”

MAKING THEIR RELATIONSHIP OFFICIAL

The two began dating shortly after but kept their relationship private. In 1999, the couple gradually began making public appearances together.

Brad's Pitt and Jennifer Aniston | Image: YouTube/ Inside Edition
Brad’s Pitt and Jennifer Aniston | Image: YouTube/ Inside Edition

By September that same year, they hit the red carpet as a couple at the Emmy Awards. Their appearance together at the 1999 Emmys marked Brad Pitt and Jennifer Aniston’s red carpet debut, and the official confirmation of their budding romance.

JENNIFER ANNISTON AND BRAD PITT GO PUBLIC WITH THEIR ENGAGEMENT

In what remains one of the most hilarious engagement revelations of all time, Aniston and Pitt crashed the stage at a sting concert. Once on Stage at the New York City event, Aniston flaunted her diamond band before the crowd, making sure it was visible for all to see.

PITT AND ANISTON’S FAIRYTALE WEDDING

Brad Pitt and Jennifer Aniston's wedding | Image: YouTube/ Channel 10
Brad Pitt and Jennifer Aniston’s wedding | Image: YouTube/ Channel 10

July 29, 2000, marked the start of a new life for Jennifer Aniston and her prince charming, Brad Pitt. They tied the knot in a glamorous Malibu wedding complete with family, friends, and fireworks. Sure enough, there was love in the air.

STARRING ON ‘FRIENDS’ TOGETHER

Another defining moment in their love story came in 2001 when the two landed roles in an episode of the sitcom, “Friends.” 

Jennifer Aniston and Brad Pitt as Will and Rachel Green in "Friends" | Image: YouTube/Hollywood Celebrity World
Jennifer Aniston and Brad Pitt as Will and Rachel Green in “Friends” | Image: YouTube/Hollywood Celebrity World

The episode, titled “The One With The Rumour,” featured Pitt as Will and Jennifer Aniston as Rachel Green. Interestingly, their characters despised each other, to the point of making up expensive rumors.

THE LOVEBIRDS SHARED PLANS OF BECOMING PARENTS

After making several red carpet appearances together, snagging several awards and nods, the public began anticipating the expansion of their family.

Four years into the relationship, Aniston finally opened up about their plans for parenthood. When asked if she had plans of starting a family with Pitt, the actress replied in the affirmative. She also disclosed that she had no problems working while pregnant, or juggling motherhood and her career.

THE BREAKING POINT

Just when it seemed things could only get better between the duo, Brad Pitt landed his life-changing role on “Mr & Mrs. Smith” alongside actress Angelina Jolie.

Angelina Jolie and Brad Pitt | Image: YouTube/Clevver News
Angelina Jolie and Brad Pitt | Image: YouTube/Clevver News

Brad’s meeting with Jolie gradually evolved into the start of something special for the co-stars, and ultimately, spelled doom for his relationship with Aniston. 

BRAD PITT AND JENNIFER ANISTON FINALIZE THEIR DIVORCE

In January 2005, Brad Pitt and Jennifer Aniston announced their mutual separation. Following the sad revelation, many speculated that the divorce resulted because Pitt had an affair with Angelina Jolie.

However, the actor debunked the claims, saying he never cheated, nor had an affair with Jolie while still married.

In a joint statement released by the former couple post-divorce, Pitt and Aniston divulged that their split had nothing to do with public speculations. Instead, the decision came from “much thoughtful consideration.”

They finalized their divorce in October 2005.

MOVING ON

Not long after their split, the duo moved on to new partners. Brad Pitt tied the knot with his new love interest, Angelina Jolie, in September 2014.

Justin Theroux and Jennifer Aniston | Image: YouTube/Cosmopolitanuk
Justin Theroux and Jennifer Aniston | Image: YouTube/Cosmopolitanuk

A year later, Jennifer followed suit, becoming actor Justin Theroux’s wife on August 5, 2015.

THE FORMER COUPLE REVIVES SPECULATIONS OF A REUNION

Two years into their marriage, Brad Pitt and Angelina Jolie divorced. Then in 2018, Aniston also ended her relationship with Justin Theroux. The time frame between Pitt and Aniston’s respective divorces raised brows at the time, with many speculating the pair may be nurturing plans of becoming a couple again.

PITT AND ANISTON REUNITE AT ANISTON’S 50TH BIRTHDAY

The friendly exes made the rumors of their reconnection more prominent in February 2019, when Pitt showed up at his ex-wife’s 50th birthday on her invite. To further crown the speculations, they had a brief exchange that left tongues wagging.

ANOTHER REUNION

They met again at the January 2020 SAG Awards, and this time, even their body languages spoke of their shared affection. Or at least, that’s what experts concluded from professional analysis.

Brad Pitt and Jennifer Aniston at the 2020 SAG Awards | Image: YouTube/Entertainment Tonight
Brad Pitt and Jennifer Aniston at the 2020 SAG Awards | Image: YouTube/Entertainment Tonight

It began with Pitt’s joke about his failed marriages during his award acceptance speech, which got Aniston laughing. And then Pitt’s affectionate expressions as he watched Aniston receive her award from backstage.

For the cherry on the icing, the two met backstage afterward, and their ten-minute exchange may have included one-too-many body contacts.

PITT AND ANISTON SPARK DATING RUMORS

Following their friendly appearances, several sources speculated that Aniston and Pitt still had unresolved feelings for each other. Furthermore, many even speculated that the duo had dated at least five times since they finalized their divorce.

The rumors became worse in April 2020 when news of their planned secret wedding in a Mexican Beach flooded the tabloids. The wedding speculations turned out to be false but did nothing to beat down the dating rumors.

Neither of the pair has since addressed the rumors, except on occasions where they claim to be “good friends.” 

In the last few months, however, both have been linked with other romantic partners. Notwithstanding, those rooting for their reconnection remain dauntless.