Brad Pitt’s Relationship With Angelina Jolie Was ‘A Different Type’ Than With Jennifer Aniston

Brad Pitt has had two high-profile marriages during the past two decades, but they were two very different relationships says Pitt’s ex-bodyguard Kris Herzog. Pitt was married to Jennifer Aniston for five years before he left her for Angelina Jolie, and their relationship lasted more than a decade and included a two-year marriage and six kids.

Brad Pitt and Jennifer Aniston
Brad Pitt and Jennifer Aniston | Photo by Kevin Winter/Getty Images

Brad and Jen were one-hundred percent happy

Brad Pitt and Jennifer Aniston had a true Hollywood romance. They started dating back in 1998 after their agents set them up, and despite their attempts to keep their relationship quiet, it didn’t take long for the world to find out that America’s sweetheart and one of the world’s biggest movie stars were an item.

They walked the red carpet together for the first time at the 1999 Emmy Awards, and just a couple of months later they announced their engagement on stage at a Sting concert.

In the days before social media, photographers did everything they could to get a photo of Brad and Jen at their lavish Malibu wedding on July 29, 2000. According to Marie Claire, it was a full-out “media circus,” and on the night of their wedding, there were fireworks in the sky.

Herzog says that Brad was “one-hundred percent happy” when he was married to Aniston, and he told Australia’s Yahoo! Lifestyle that he never heard the couple fight. He added that Jennifer loved Brad with “all her heart,” and never saw her look at other guys.

“I never heard rumors of cheating,” said Herzog. “I never heard anything bad between Jennifer Aniston and Brad Pitt before he met Angelina Jolie.”

Brad Pitt’s life-changing role

When Brad took the lead role in the 2005 action flick Mr. & Mrs. Smith, he had no idea how much it would change his life. The movie made nearly $500 million at the box office, but it was meeting his co-star, Angelina Jolie, that changed everything.

Brad and Angie ended up falling love on set, and she told Vogue that after a few months of working with Brad Pitt she couldn’t wait to get to work.

“We just became kind of a pair. And 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,” said Jolie. 

Aniston didn’t appreciate Jolie talking to the press about falling in love with her husband.

“There was stuff printed there that was definitely from a time when I was unaware that it was happening,” she told Vanity Fair. “I felt those details were a little inappropriate to discuss. That stuff about how she couldn’t wait to get to work every day? That was really uncool.”


Not long after Brad Pitt and Aniston announced their split in January 2005, Pitt and Jolie went public with their relationship. For the next eleven years, they were Hollywood’s most famous couple because Angelina wanted it that way.

“It was, ‘We are the most powerful celebrity couple in the world,’ and that was primarily Angelina pushing the public image,” said Herzog.

Brad and Angie had six children together and eventually tied the knot in 2014. Their relationship came to a shocking end in September 2016 after Angelina accused Brad of child abuse.

Brad Pitt and Jennifer Aniston are just friends

While Brad and Angie were together, Jennifer moved on with Leftovers star Justin Theroux. But their relationship didn’t last either, and they called it quits in February 2018. Once Brad and Jen were both single, fans were hoping that the two would rekindle their romance.

The rumor mill went into overdrive earlier this year when Brad showed up for Jen’s 50th birthday party, but when a paparazzo asked Brad Pitt if he and Jen were getting back together, he laughed it off and said, “Oh, my God.”