Does Brad regret how he split from Jen?

February 14, 2019

When they met it was a setup, by their agents, and Jennifer Aniston told Diane Sawyer that they both felt like it was meant to be on that first date.

They married in the summer of 2000 and all seemed well, but then in the summer of 2004 Brad Pitt starred in Mr. & Mrs. Smith with Angelina Jolie and they fell for each other during filming. The split was announced as amicable and by 2005 they were divorced.

But it wasn't long before it became clear Jen hadn't been told the full story and later she talked about being unaware of what was really happening, when it actually happened. Remember she described Brad as "missing a sensitivity chip." Brad & Angelina thought they were on a secret getaway to Kenya, but they were photographed and revealed several months before the divorce was finalized.

Fast forward to 2019 and it seems Brad now admits he regrets how he ended it; a source told Us Weekly that he "wishes he'd handled the end of the marriage in a more thoughtful manner."

This interview with Diane Sawyer at the time of the split is still interesting. She's great at asking those deeply personal questions no one wants to answer and you can't help but notice his defensive nature. Skip to the 2:50 mark if you want to go right to the nitty-gritty.