20 Things That Uncover Jen And Brad’s Real Relationship

If you're like us, you're probably still hoping for Jen Aniston and Brad Pitt to reconcile. We totally feel your pain! We couldn’t believe it when these two got divorced in 2005! In a way, it kind of seemed like these two Hollywood icons were made for each other. But nothing lasts forever, not even in Tinsel Town. Of course, that doesn’t mean there aren’t any flames still sparking whenever they run into each other. And yes, apparently, it's not just a rumor. Jen and Brad have actually bumped into each other!

They stay in touch and are on speaking terms, but as far as we know, there’s nothing going on between them. Well, that's what they want the world to believe! It’s hard to deny that these two could find their way back to each other someday if they really wanted to. There’s plenty of history between them, and we do mean plenty!

In fact, days after announcing she had split from Justin Theroux, news broke that Jen still kept certain mementos that reminded her of her life with Brad. As for Brad, there are rumors that he’s been dating Charlize Theron, but nothing’s been confirmed yet.

So, while we cross our fingers and hope that Jen and Brad will give their relationship another try, let’s take a look at some facts about their relationship.

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20 Their Managers Set Them Up On A Date In 1998


Jen and Brad first met in 1994 and they can thank their managers for it. Jennifer told Rolling Stone that Brad was just a sweet normal guy from Missouri. Unfortunately, he was still dating Gwyneth Paltrow. That relationship ended, though. Brad and Gwyn broke up in 1997. In 1998, Jen and Brad’s managers played matchmakers and set them up on their first date and they had a lot of fun.

In fact, Jen explained that the date was a bit weird because they both seemed to feel totally comfortable with each other. From that point on, it became clear that they both saw the possibility of a future together.

19 Jennifer Admitted That She Didn't Know If Brad Was The Love Of Her Life, But Said They Had Something Special


Jen admitted during an interview with W magazine that she wasn't really sure if Brad was the love of her love, but she did say that the two lovebirds had something special. To this day, she claims she has never met someone she can call the love of her life without a shadow of a doubt. But he was certainly a big love in her life, and that’s not something a gal gets over right away.

When they were married, he managed to keep her anchored in an otherwise nutty and fast-paced Hollywood. But Jen also loved the fact that Brad was the type of guy who knew the real Jen, and that really made her feel at peace.

18 In 2003, Jen Admitted That Brad And Her Used To Fight, But That's Only Normal, Right?


By 2003, Jen had admitted to W magazine that she and Brad had figured out more or less how to live together. But she also said that they had had a lot of arguments like most couples do. Not that there’s anything wrong with that. After all, how many couples can say they haven’t had a few disagreements here and there?

But Jen doesn’t like fighting to the point where two people are shouting at each other. It really gets under her nerves. Jen is the type of gal who would rather find a solution to a problem that allows both parties to move forward.

17 Jen Never Seemed Interested In Having Children, But She Claimed She Was Ready To Start A Family With Brad


Just as the sitcom Friends was about to end, Jen sat down with The Guardian to discuss the possibility of having babies with her hunky actor husband, Brad. This undoubtedly blew a lot of people away because she never seemed interested in having any kids. But she felt that she was starting to feel like it was time to start a family.

She wasn’t worried about how becoming a mom would affect her career. She knew that actresses can work while being pregnant and even after they've given birth. But while she was looking forward to slowing down and having kids, Brad was busy finishing up Mr. And Mrs. Smith and he still had Ocean’s Twelve to do.

16 Brad Admitted Having Issues With Substances, Which May Have Clouded His Judgment

Instagram / @leonardodicaprio

It’s hard to say what the final straw was that broke these two up, but in an interview with Esquire, Brad spilled his heart out and confessed he was having issues with controlled substances at the time of their divorce. In fact, he felt that his partying lifestyle had left him completely burnt out. At some point, he realized he needed to make a major change before the damage was irreversible.

Unfortunately, this major epiphany didn’t just mean he’d be saying goodbye to his problems with addiction, but also to his relationship with Jen. After that, all they had left to do was make an official announcement.

15 After Their Very Public Divorce, Jennifer Claimed The Two Had Exited Their Relationship As Beautifully As They Entered It


There were a lot of rumors regarding whether Jen and Brad were dunzo before they officially called it quits. After a couple of months, the former power couple released a statement that confirmed they were in the process of putting an end to their seven-year marriage. And we all know how it goes. No one goes from being in love one day to wanting a divorce the next one. These things take time.

Jen and Brad gave a statement to People in which they announced the heartbreaking news. But they also mentioned how they had given their decision thoughtful consideration and how they were committed to each other as friends. Then, in an interview with Vanity Fair, Jen said that they had exited their relationship just as beautifully as they had entered it.

14 Jen Confessed In An Interview That She Went Through Different Stages Of Grief After She Split From Brad


During a 2005 interview with Vanity Fair, Jen confessed that she had a hard time dealing with her split from Brad. She went through the same stages of grief you would expect someone to go through after losing a loved one. She experienced sadness as well as pain. To make things worse, she had to rise above all that while being under the constant scrutiny of the public eye and media.

She felt like an egg that had been cracked open. But she somehow managed to handle it like a boss and shine like the star that she was and continues to be.

13 When Angelina Jolie Met Brad, She Said They Were The Last Two People Who Were Looking For A Relationship


In 2007, Angelina Jolie told Vogue that she was totally okay with being a single mom. When she met Brad, she knew he was with someone he loved and respected. So, everyone was pretty happy with the status quo, and neither Angelina nor Brad were really looking to start a relationship.

But while filming Mr. and Mrs. Smith, the two of them were brought closer together. Suddenly, they found themselves locked in a friendship that was taking them towards an unforeseen destination... love. Before either of them realized what was really happening, they became more than friends. They became Mr. and Mrs. Brad Pitt.

12 Brad Felt Like He Wasn't Living The Life He Wanted Back When He Was Married To Jen

Jim Smeal Getty Images

According to Brad, things weren’t exactly perfect when he and Jen were together. During his marriage, he was feeling mentally crushed while trying to avoid his hectic celebrity life. He often found himself sitting on a couch, using anything he could to escape his boring existence.

In 2011, Brad told Parade that he was interested in finding a movie project about someone living an exciting life because that was something he didn’t feel like he had at home with Jen. He added that he was pretending that his marriage was something that it obviously wasn’t, and it disrupted the bond he and Jen had.

11 As Time Went By, Jen And Brad Became Totally Different People

Instagram / @justintheroux

Jen and Brad were grilled by the media over what their relationship was like post-breakup. But even if the media claimed these two were getting back together, the former power couple stayed hush. Most media sources reported that with the exception of a few friendly texts here and there, Jen and Brad had virtually no contact.

Fans saw a glimmer of hope when Jen split from her husband Justin Theroux in 2018. But the moment was fleeting after a source told People magazine that it was unlikely that Jen would try to get back with Brad because they weren’t technically friends at all. In fact, they hadn’t really seen each other in a while. But were they still thinking about the good old times?

10 When Jen Divorced Justin Theroux, He Found Romantic Notes That Brad Had Written To Her

Photo by Evan Agostini

Brad may no longer be in Jen’s heart but she hasn’t completely let go of the past, according to her ex Justin Theroux. Jen and Justin released a statement to USA Today that their two-year marriage was over but they had decided to remain friends.

Shortly after they broke up, a source told Us Weekly that Theroux had discovered something Aniston may not have wanted the world to know. She had kept the post-it notes that Brad had written to her while they were still married. Some of the notes said sweet things like ‘Miss you already’ and 'You looked nice tonight.’

But that's not all!

9 Brad Felt The Need To Track Jen's Number And Text Her After He Split From Angelina


After his public and turbulent split from Angelina, Brad had the urge to text Jen in March 2017. A source told Us Weekly that Brad had somehow tracked Jen’s phone number down so he could wish her a happy birthday. Isn’t that adorable? As you can imagine, the two of them hadn't been in touch for years, so Jen probably never saw it coming!

The source also added that Brad was having a rough time after his split. This led to an exchange of texts where they both reminisced about the good times. But given the way he had ended things with Jen so long ago, it’s a miracle she even responded to him. Many people even wondered if he had ever apologized.

8 After Being Estranged For Years, Brad Told Friends That He Regretted How He Treated Jen After The Divorce


An insider told Us Weekly that Brad deeply regretted the way he handled his divorce from Jen. In fact, he wished he would have found a more thoughtful way to split up, not that this would have been easy. Breakups are horrible, whether you're being gentle about it or not. It’s rare that people can walk out of a relationship without getting hurt, even just a little bit.

But the source also said that Brad did ask Jen for forgiveness and that she gave it to him. Although he can’t go back in time to fix things, he definitely seems to be trying to be a better friend to Jen.

7 Brad Even Contacted Jen After Her Mother Passed Away


She might have been his ex, but Brad still had a soft spot in his heart for Jen. When he and Angelina broke up in 2016, rumors that Brad and Jen were rekindling their romance flooded the media. It was hard not to jump on the bandwagon and want to believe this was a possibility.

After all, Brad reached out to Jen shortly after the loss of her mother, Nancy Dow. And she was truly touched that he contacted her during one of the toughest moments of her life. It meant the world to her and when the time came, she would repay him with the same kindness he had shown her.

6 Not Too Long Ago, Jen Contacted Brad To Let Him Know She'd Be A Character Witness At His Pending Custody Battle

Instagram / @bradpittoffcial

Us Weekly reported that Jen and Brad were texting in 2017 and there was a good reason for that. He was confiding in Jen about his split from Angelina. A pending custody battle was bound to ensue between Brad and the Maleficent star. Things got so bad that the FBI investigated claims that Brad had been verbally and physically disrespectful to one of his kids while on a private jet on their way from California to France.

So, Jen offered to be a character witness to counter some of the claims made against him by Angelina. In the end, the FBI cleared Brad of any wrongdoing.

5 Brad Made A Surprise Appearance At Jennifer's 50th Birthday

Turning 50 is a big deal, so Jen decided to celebrate this milestone at the Sunset Tower Hotel in Los Angeles, California. There were tons of VIP guests like Orlando Bloom, Katy Perry, George and Amal Clooney, and Jason Bateman.

But 45 minutes after Jen arrived at the party, Brad made a stellar appearance that stopped everyone in their tracks. He was surrounded by his security team and seemed to be in a great mood as he walked into the hotel wearing a hat and a dark shirt. Soon, Jen and Brad fans from all over the world were squealing with joy when they heard the news.

4 But Brad Wasn't The Only Ex-Partner Who Came To Jen's Party


Brad may have been an important ex in Jen’s life, but he wasn’t the only ex who showed up at her big bash. She made an effort to ensure that everyone who had made some kind of impact on her life was there to celebrate her 50th birthday. She even invited Katy Perry’s ex John Mayer and Brad’s ex, Gwyneth Paltrow.

Basically, it was a star-studded event where present and past relationships converged in one place. Fortunately, everyone was cordial to each other and no fights broke out. But one notable person was missing at the party and that was Jen’s other ex, Justin Theroux.

3 Staying Friends With An Ex Is Hard Work, But Jen And Brad Seem To Be Pretty Good At It


It’s not easy staying friends with an ex. There are a lot of obstacles to overcome as most breakups don’t end well. Someone usually winds up with a broken heart, and it’s tough to let the past go and allow bygones to be bygones. But Jen’s 50th birthday party was a celebration of her life and Brad was a huge part of that.

She had debated with her friends whether she should invite him or not, as Just Jared reports. In the end, she was happy he showed up. Imagine all the drama if he had just crashed her 50th birthday bash! That being said, it would've made one iconic Hollywood moment, right?

2 But Are They Heading Towards A Reconciliation?


You’d think that being the woman of the hour would mean you wouldn’t have to do a lot of work, but Jen was busy making sure all of her guests had a great time. The hotel terrace’s pool and bar were decorated with tons of candles and white flowers. They even hired a DJ for this epic occasion. Everyone was in the mood to have fun, wish Jen a happy birthday and offer up toasts. But when she saw Brad, she didn’t evade him. She greeted him with a big hug and stayed and chatted for a while.

Insiders told E! News that the two former lovebirds are neither dating nor headed towards a reconciliation.

1 That Being Said, Jen Has A Soft Spot For Brad, So No One Can Really Tell What's Going To Happen In The Future


Things didn’t turn out the way Jen and Brad thought they would when they promised to love each other forever. But she still feels quite fortunate to have experienced her first marriage. It gave her an insight into what married life was all about. So, as far as Jen goes, she has no plans of feeling bad about the fact that her marriage didn’t work out. They learned a lot from each other about having fun and helping one another over the years.

She still considers Brad to be a fantastic guy. So, all in all, there’s still a soft spot in Jen’s heart for Brad. No one can really say what the future holds for these two. We'll just have to wait and see!

Sources: Rolling Stone, W magazine, The Guardian, People, Vogue

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