Rare Photos of Brad Pitt and Jennifer Aniston

Brad Pitt and Jennifer Aniston were one of America’s favorite Hollywood couples. Though their split was more than a decade ago, now that Brad has moved on from Angelina, it’s the prime moment to look back on the photos you didn’t see when they were together.

In The Cards

From the moment Brad and Jen debuted their relationship on the public stage, fans were enthralled by the idea of the perfect Hollywood power couple. Many are still hoping there’s a chance to rekindle that flame.

The First Look

Unlike many other Hollywood couples, including Brad and his second wife, Angelina Jolie, Jennifer and Brad didn’t have a glamorous Hollywood meeting on a film set. The pair were both popular in their own right, as Jennifer was starring in the consistently popular Friends, and Brad has recently starred in both Fight Club and Seven. Despite their high profile career, both were single, so their publicists stepped in and set the two up on a blind date.

Dinner And A Movie

You might expect first dates between celebrities to be the stuff that glamor is made of. You’re more likely to envision stars being wined and dined by their prospective romances, or being whisked off on a whirlwind visit to a foreign locale. Brad and Jen may have been at the top of their game, but their first date was much more low key. The pair were happy to spend their evening at Brad’s place, possibly even watching a movie while they “chilled.”

Shooting For The Stars

Jennifer Aniston wasn’t Brad’s first high profile relationship. The leading man, whose looks have often been honored on the cover of People magazine, had a slew of famous leading ladies in his life from before he took up with ‘America’s Sweetheart.’ Some of Brad’s earliest Hollywood girlfriends include Gwyneth Paltrow, Christina Applegate, Juliette Lewis, and Geena Davis. Almost all of his previous girlfriends were women he’d met on set while working with them on various film projects.

Getting Serious

While Brad was off dating as many Hollywood stars as he could, Jennifer was already showing that she was much more of a relationship girl. In the years before she was introduced to Brad, Jennifer was involved with the actor Tate Donovan, who even had a chance to play her onscreen flame, Joshua, for several episodes of Friends. The pair got engaged after several years of dating, but they would never end up walking down the aisle together.

Facing Her Again

It seems that none of Aniston’s relationships come easy. Her former beau was only cast in Friends right around when their relationship began to hit the rocks. Even as their engagement was coming to an end, Donovan had to face his ex every single day, as they worked together playing romantic interests on set. In recent years, he’s begun speaking out about what a difficult time that was for him, sharing in interviews that working with Jen during a break up was awful.

Palin’ Around

Brad had an earlier engagement of his own several years before he would be set up with Jen. During the mid-’90s, Brad was one half of a very different “it” couple when he dated Gwyneth Paltrow. The two spoke openly about their love for one another, and even got engaged, before calling it off in the summer of 1997. In reflecting back on that time, Paltrow states that she was only 22 when they met, hardly old enough to make such a serious commitment as marriage.

Letting Secrets Slip By

For two big stars, it’s often difficult to keep the media in the dark about new relationships, but somehow, Brad and Jen were together for months before taking things public. Their very first outing as a couple was at a local concert, where unsurprisingly, the paparazzi began snapping away. One of the shots that made it to press was a sweet image of Brad with his arms around Jen, while she reached up towards his face.

Following Her Instinct

When reflecting back on the early days of her relationship with Brad, Jennifer told Diane Sawyer that she knew from the beginning the two shared something special. “It was weird…” Jen recalled, discussing their first date, “That was a really easy evening. It was really fun.” It seemed that with each other, their past heartbreaks just melted away when they were together. Even so, they were still tried to keep things under wraps for as long as they could.

Love Shines Through

During 1999, when Brad and Jen were still half-heartedly denying their romance, Lisa Kudrow, one of Jen’s Friends colleagues, was asked to comment on the pair. She told Rolling Stone, “Jennifer’s a lot more peaceful now, like a woman who’s in a good relationship.” She continued, adding, “There’s not a lot to say about them because there’s no problems. They’re both light-years ahead of themselves. You know how your grandparents have a certain perspective about life? They’ve got that now.”

Prom King And Queen

One of the biggest reasons Pitt and Aniston were so beloved as a couple had to do with their image as the two most popular kids in school. That they were both riding high in their respective careers only added fuel to the fire. Everyone wanted to know what it was like for America’s two most popular actors to fall in love. Aniston especially though was determined to remain tight-lipped. “I’m not withholding,” she told Rolling Stone, “[J]ust preserving something that’s mine.”

Promoting The Positive

Most tabloid speculation about celebrity couples is often a study of reading disaster into the most benign of situations. Brad and Jennifer were a different animal altogether, as most rumors purported that the relationship was moving even faster than the stars were admitting. People close to Jen, however, had been worried when they first joined together that Brad wouldn’t be a good influence on the star, and therefore discouraged the relationship – until they got to know him, that is.

Making A Grand Debut

When Brad and Jen were finally ready to make their first big public appearance, they figured they might as well do it at an event where people were already going to take notice. As the red carpet for the 1999 Emmy’s was rolled out, Brad and Jen decided to walk down it arm in arm, and the fans, who had been waiting for this moment ever since their relationship was first hinted at, couldn’t get enough of the couple.

Engaged And Center Stage

The media absolutely blew up the first time the pair made a red carpet debut arm in arm. Despite the frenzy they inspired, Brad and Jennifer managed to pull off an under the radar engagement, which absent from social media, remained private until they took the stage at a Sting concert. With a massive rock shining on her finger, Brad and Jen were happy to finally clue in the rest of the world that they’d soon be tying the knot.

Breaking The Deal

It should come as no surprise that when Brad got engaged to the woman he thought was the love of his life, he wanted to get her a one of a kind ring. He hired a jewelry maker under the circumstances that the custom-made ring would never be reproduced, especially because the design was one dreamed up by Brad himself. To the couple’s dismay, the company, Damiani International Jewelers, quickly began selling copies. Brad and Jen quickly filed a lawsuit to stop the sales.

A Complicated Affair

Planning a wedding is almost never a walk in the park, but it becomes even more difficult when you have the paparazzi trailing your every move. Pitt and Aniston were determined to keep their nuptials as private as possible,  which entailed spending $100,000 just on security. Even Jen’s besties from the set of Friends were required to don special badges in order to be allowed through security. The feat was even more impressive given that their guest list totaled 200.

Notably Absent

For the multitude of guests who joined Brad and Jennifer on their special day, one guest was expressly not invited: Jen’s mom, Nancy Dow. The two had long had a strained relationship, which was made even more tenuous when Nancy published a tell-all book about her daughter. Instead of inviting extra stress into her big day, she chose to keep her mom at arm’s length. They wouldn’t reconcile until after Brad and Jen called it quits on their marriage.

Food For The Soul

Brad and Jen were slated to have the wedding of the year, if not the century, and yet it had only just begun. One of the attractions the A-list couple decided to add to their big event was a 40-person gospel choir that would serve as entertainment. That wasn’t enough for them though. Even with the excellence of the gospel choir, for some contrast, the pair also invited Melissa Etheridge to give a performance at the wedding.

Ending With A Bang

As their fairytale evening wound down, Brad and Jen had a special surprise planned for their guests. With a stretch of the Malibu shore shimmering behind them, the happy couple wanted to end their nuptials with a spark that showed just how strong theirs was. Before the guests began to depart, a fireworks show showered over the sea, making it the perfect ending to a wedding for Hollywood royalty. Of course, it could also have symbolized things to come.

Relishing The Golden Hour

Jennifer had many fond memories of her wedding day. In 2001, she told Rolling Stone, “I had those typical jitters the day before my wedding, but the day of, I was just excited in a good way. The nice thing about weddings now is it’s not just a chick thing. It’s a team effort. The stereotype used to be men grumbling, like, ‘Why are you making me do this?’ There’s nothing more moving than seeing a man cry at his own wedding.”

Disappointing The Crowd

As Jen continued her run in the ever popular Friends, the producers had a treat for long time fans, especially those who continued to inhale any news related to the golden couple. Brad Pitt made a famous guest appearance on Friends during one of their beloved Thanksgiving episodes. Though his episode was highly anticipated, in the end, his character, who hated Jen’s character Rachel, fell flat. Pitt’s performance was lambasted by critics and considered to be one of the worst guest appearances on the show.

Cracks In The Ceiling

As much as America loved Brad and Jennifer together, by 2004, it’s clear the couple was treading on thin ice. For all the factors that contributed to their split, Jen explained that there was one thing that really trumped everything else. When Friends ended in 2004, Brad wasn’t by her side. ”[H]e just wasn’t there for me,” she confessed in a profile of her that was published in Vanity Fair in 2005. Wrapping up Friends was a big transition for Jen, and she didn’t have emotional support.

Nightmares From The Past

As a child, Jen had endured a fairly nasty divorce when her parents split up. “I had no idea,” she admitted. “I didn’t grow up surrounded by any form of marriage.” For her, “just finding someone who was your best friend, who you could grow with and enjoy the passage of time,” sounded like it would be enough. Jen had no idea of what marriage could or should be like, as her parents’ union had been a horrifying example.

Taking Shots

As with any relationship, there are two sides to any story, and Brad’s certainly differed distinctly from Jen’s. For all of the hurt he may have incurred, his words in a 2011 interview to Parade cut the deepest. “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 had something to do with it. Trying to pretend the marriage was something that it wasn’t.”

New Woman In Town

Not only were America’s favorite couple splitting up, it didn’t help that it appeared Brad had left his sweet wife for Angelina Jolie, whose reputation stood in stark contrast to Jen’s. Although Brad and Angie continued to insist that their relationship hadn’t been physical before Brad’s divorce was finalized, some reports surfaced that say the two were seen kissing on the set of Mr. and Mrs. Smith, long before Brad and Jen actually decided to end their marriage.

Make Room For Baby

Of the most hurtful accusations lobbed at Jen for her role in the split, the insinuation that Brad left her because she wouldn’t take off work to start a family cut the deepest. Jen reiterated in her Vanity Fair interview, “A man divorcing would never be accused of choosing career over children.” She later added, “I’ve always wanted to have children, and I would never give up that experience for a career. I want to have it all.”

Bringing Up The Brood

Neither Brad Pitt or Jennifer Anniston planned to have a childless marriage, but it seemed they had some differing ideas as to how big their family would be. “I always thought two or three children,” Jen revealed in a candid interview with Vanity Fair, which was released four years before her next profile, “but Brad’s definitely seven. He loves the idea of a huge family.” Unfortunately for Jen, her plans for children wouldn’t come to fruition, though Brad’s would.

His Experimental Phase

Jennifer may have done what she could to remain polite about Brad, but even before their split, it appeared he didn’t have the same sensitivity. In his own Vanity Fair profile, which was released before they even separated, Brad told the interviewer that he viewed his marriage to Jen as an “experiment.” He even speculated that were they to split, it would be an amicable move, a view which failed to take into account just how hurt Jennifer would be.

Paging Mrs. Smith

For all of the rumors and speculation that were fueled in the immediate months following Brad and Jen’s divorce, one of the best was a rumor that Jen was using the alias, Mrs. Smith, while staying in a Chicago hotel. The rumor turned out to be false, though Jen did say, “I wish I’d thought of it” when presented with the rumor. The only truth held within was that she was indeed using a funny alias at the hotel.

Keeping Tabs

Though the report went otherwise undiscussed in Aniston’s candid Vanity Fair interview, according to People, a friend of Jen’s shared that Aniston still called Pitt from time to time after their split, despite the fact that he had publicly revealed a relationship with Jolie a little too soon. One of the reasons given is that Pitt had been in the hospital for meningitis, during which time, she made a “couple” of phone calls in order to check in on his health.

Harder Than The Rest

Jennifer remained stoic during the aftermath of her divorce, partially by keeping her head down as she retreated to a new home in Malibu. There was only one piece of the equation that could immediately bring Jen to tears. Even by September 2005, reports were flying that Brad and Angelina were expecting a child together. For all the speculation about when Jen would conceive herself, hearing that the new couple was already starting a family was too much for her to handle.

Words Taken To Heart

As Brad and Jen’s separation continued to be headline news, the one rumor that wouldn’t quit was that Brad had been cheating on Jen with Angelina. Jen, however, wanted nothing to do with those rumors. During her sit down with Vanity Fair she divulged,  “I choose to believe my husband. At this point, I wouldn’t be surprised by anything, but I would much rather choose to believe him.” Even so, Aniston was a pool of hurt.

Lurking In The Shadows

As Jen worked to heal from her break up, she found it prudent to drop out of the spotlight that had shined so intently on her while she was with Brad. She moved out of their mansion into a much cozier home in Malibu where the Pacific Ocean lapped at her back porch. She found the change to be a soothing change, and one that was much needed in order to preserve her fragile mental health.

Caught In The Act

Despite maintaining that he and Angelina had remained only friends until after Brad and Jen had split, one of Angelina’s former bodyguards alleged that they weren’t being totally honest with the public. In a statement made to US Weekly he said, “I caught them several times in each other’s trailers making out. I wasn’t shocked at all when they got married years later.” The pair may have claimed innocence, but no one would be surprised if this was really the case.

Finding The Total Package

While Brad was busy building a family with Angelina, Jen was bouncing from man to man, hoping to find love. In 2010, Jen had the chance to be the Angelina of the situation, when she began dating Justin Theroux, one of her costars in the film Wanderlust. When the two married in 2015, fans hoped that Jen was finally going to have her happy ending, even though her original Prince Charming proved to be more of a dud.

Spirited Away

Over the years, the vitriol many of Aniston’s fans felt towards Jolie began to wane, but when her separation from Pitt was announced in 2015, many couldn’t help but feel that it was some sort of vindication for Jen’s ordeal. After being together for over a decade, Brad and Angelina were splitting up only two years after they succumbed to their six children’s urging that they get married. Many sources blamed Brad for events that had led to the split.

A Family Dispute

One of the most surprising reports alleged that Brad had gotten into a big disagreement with his oldest son Maddox, who is still only a teenager, while they were on a private flight. Though authorities were investigating wrongdoing on Pitt’s part, it seems the supposed altercation began when Maddox was trying to defend Jolie. Shortly thereafter, Jolie filed for divorce, ending the relationship that was often looked upon as a stain on Brad’s previous marriage with Jennifer Aniston.

Digging Into The Darkness

Following his second divorce, Pitt had a lot of self-reflection to do. When he was finally ready to open up to the public, he revealed an ongoing struggle with sobriety that had taken over his life. He explained to GQ, “I can’t remember a day since I got out of college when I wasn’t boozing … I mean, I stopped everything except [drinking] when I started my family. But even this last year … I was [drinking] too much. It’s just become a problem.”

Double Trouble

Given that Brad shares six children with Angelina, it’s only natural that their divorce would be more complicated than his first. However, he never anticipated just how nasty it would be as Angelina began to fight him for custody. Throughout the battle, Brad maintained that he wanted to hold on to a relationship with his children, which Angelina was reluctant to agree to. The dispute would drag on for more than a year and a half after they announced their separation.

Slips Of The Past

When Brad announced his split, Jen was finally happily married to Justin Theroux, a relationship that came to an end only a few months ago. It came to light after they announced their split that Jen had held on to some sweet post-it notes that had been written to her by Pitt during their marriage. While it might not have been a deciding factor, it seems some of Jen’s nostalgia for her first husband contributed to the breakup.

Making Amends

Now that Brad and Jen are both not married for the first time since their 2005 divorce, many fans are hoping that there’s a chance they’ll get back together, though it seems highly unlikely. In any, case Brad has done a lot of reckoning with himself, which seems to include apologizing to Jen for how he treated her towards the end of their marriage, especially with regards to the beginning of his relationship with Jolie. For Jen, it seems to be enough.