Woulda, Coulda, Shoulda! Celebrities Who Regret Their Divorce: Ben Affleck, Kris Jenner and More

Kris Jenner

Kris Jenner and Robert Kardashian, Sr. met in 1973, and later married in 1978. The couple had four children together before they divorced in 1991. She later admitted to having an affair which played a large part in her and Robert’s decision to split.

“It made me feel young, attractive, sexy, and alive. Along with these feelings came a wave of nausea. I actually wanted to throw up at the same time. Because it dawned on me that I had not felt that way with Robert for years,” Kris wrote in her memoir Kris Jenner… And All Things Kardashian.

However, the reality TV star blamed a large part of the divorce on her affair and ultimately regretted the decision.

In an interview with Objectified, Kris told reporters, “When I look back on it now, probably one of my biggest regrets in my life is that that marriage fell apart.”

Samantha Lee

The Fast and the Furious franchise star Tyrese Gibson first met his now ex-wife, Samantha Lee, at a charity event in Atlanta, Georgia, and they got married less than a year later on Valentine’s Day in 2017. However, in December 2020, the couple announced they were divorcing.

Later, Samantha claimed that the people that were supposedly helping her with her relationship struggles ultimately played a part in the end of her marriage.

“The truth about the matter is that if I had different people in my ear at that time I would not have made that decision,” Samantha told hosts in a guest appearance on the “Hardly Initiated” podcast.

Ryan Phillippe

Ryan Phillippe and Reese Witherspoon were one of the most popular couples of the ’90s. They starred in the hit film, Cruel Intentions, and many people believed that’s where the couple’s romance began. However, they actually met at a birthday party in 1997 and had already been dating by the time they began filming the movie. They tied the knot in June 1999, and she gave birth to their first child, a daughter named Ava, in September of that same year. They welcomed their son, Deacon, in October 2003. Three years later, Reese and Ryan publicly announced they were separating.

In 2008, Ryan opened up about the divorce with W Magazine and called it “the darkest, saddest place I’ve ever been.”

“There were a good four or five months of not being able to get out of bed,” the Crash actor said. “It was the worst time of my life.”

Jennifer Aniston

If there was one couple dominating the headlines in the year 2000, it was Brad Pitt and Jennifer Aniston. Jennifer’s role in the sitcom Friends caused her career to skyrocket, and Brad had already made his mark on Hollywood with films like Fight Club and Seven.

The couple said “I do” in July 2000, but it was only five years later when they announced their separation. Jennifer officially filed for divorce in March 2005. However, The Morning Show star admitted that she did have some regrets.

“There’s a lot I would probably do differently,” Jennifer told Vanity Fair in October 2006. “I’d take more vacations — getting away from work, enjoying each other in different environments. But there was always something preventing it; either he was working or I was.”

Courteney Cox

Courteney Cox and David Arquette first met on the set of the hit slasher film Scream in the mid-90s. They went on to star in several more films within the franchise, and the couple married in 1999. David and Courteney welcomed their daughter, Coco, in 2004, but over a decade after walking down the aisle, the pair announced they were going their separate ways. Regardless of the divorce, they’ve stayed friends over the years, but Courteney confessed that she did have some regrets.

“In divorce you always have regrets,” Courteney told More Magazine in February 2014. “We were married for a long time, so it’s not like we didn’t try.”

Ben Affleck

Before Ben Affleck was married to Jenny From the Block, he had tied the knot with Jennifer Garner. Jennifer and Ben met on the set of the 2001 film Pearl Harbor, but the pair didn’t start dating until years later. They teamed up again in the movie Daredevil in 2003, and by 2004 they were in a relationship. The Good Will Hunting star proposed in April 2005 and walked down the aisle just two months later. They went on to have three children together, but by 2015, Jennifer and Ben decided to call it quits. Their separation announcement came just days after their 10th anniversary.

However, years later, it appeared Ben never quite got over his relationship with Jennifer ending. Despite finding love again with J. Lo, Ben told The New York Times in May 2023 that his divorce was “the biggest regret of his life.”