There Was 1 Major Difference Between Brad Pitt’s Marriage to Angelina Jolie Compared to Jennifer Aniston

As far as we know, Brad Pitt is single right now. But his relationship past includes two very high-profile marriages — and later, two messy divorces — from Jennifer Aniston and Angelina Jolie. The common denominator in each? One man who has admitted to making more than a few mistakes along the way.

Brad Pitt and Jennifer Aniston | Kevin Winter/Getty Images

There are both similarities and differences in Brad Pitt’s marriages to these two women. If Pitt could go back in time, he’d probably make some different choices. Here are a few of the major differences between Brad Pitt’s marriage to Angelina Jolie compared to his union with Jennifer Aniston.

Brad Pitt fell in love with Angelina Jolie while he was still married

Maybe the most defining factor of Brad Pitt’s relationship with Angelina Jolie is that it started as an affair.

Neither Pitt nor Jolie was looking for love when they fell for each other in 2004. The pair met on the set of the movie Mr. & Mrs. Smith while Pitt was still married to Aniston. Later, Angelina Jolie opened up about their surprising romance during an interview.

“Brad was a huge surprise to me. I think we were both the last two people who were looking for a relationship. I certainly wasn’t,” Jolie admitted.

Expected or not, these two fell quickly and deeply in love. Within a year, Aniston and Pitt were divorced and he moved on to get serious with Angelina Jolie.

Brad Pitt and Angelina Jolie
Brad Pitt and Angelina Jolie | Anthony Harvey/Getty Images

Jolie and Pitt were together for longer, but married for less time

Brad Pitt and Jennifer Aniston met in 1999 and married in 2000 after a whirlwind relationship. Their wedding was a lavish Malibu affair that reportedly cost around $1 million. They were married for five years total, divorcing in 2005.

Meanwhile, Brad Pitt began a hot and heavy relationship with Angelina Jolie in 2005 though they didn’t marry until close to 10 years later. The pair once famously said they wouldn’t tie the knot until “everyone could legally marry,” including same-sex couples.

They got engaged in 2012 and married in 2014. Brad Pitt and Angelina Jolie filed for divorce just two years after marrying, in 2016.

Pitt and Aniston never had any children

Though the world was on baby watch since the moment Brad Pitt and Jennifer Aniston tied the knot, these two never had any children of their own during their five-year marriage. That’s vastly different than the child-filled life of Pitt and Jolie.

Jolie Pitt family
Jolie Pitt family | Jun Sato/WireImage

When the Brangelina became a thing, Jolie had just adopted son Maddox from Cambodia. Over the course of their relationship, Pitt and Jolie would go on to have three biological children (First Shiloh and later twins Vivienne and Knox) and adopt two more children (Pax and Zahara).

If you’re keeping count, that’s six kids all together.

Their post-divorce lives are way different too

One intriguing thing about post-divorce Brad Pitt with each of his exes is how differently things have gone. With Jennifer Aniston, Pitt wasn’t that friendly with her at first, and she even said he was “missing a sensitivity chip” after some comments he made about how enamored he was over Jolie while he was still married.

Brad Pitt and Jennifer Aniston
Brad Pitt and Jennifer Aniston | Boris Horvat/AFP/Getty Images

However, their relationship has improved over the years and now the two are friendly. Brad Pitt was even spotted at Jennifer Aniston’s 50th birthday party a few months ago.

For Brad and Angelina, things went a lot differently. While the split seemed amicable at first, it gradually devolved into an epic custody battle that required mediators and a huge amount of compromise.

There’s no saying one relationship was better than the other. But they sure were different!