Celebs Who Have Regrets About Getting A Divorce

With the spotlight on them, every chapter in a celebrity's life is magnetized. Whether these A-listers are tying the knot, starting families, or getting divorced, it's front-page news for the rest of the world. There's a fascination that comes along with Hollywood stars whose lives are on a pedestal. Though they have immense amounts of power and social influence, they fall in love and get their hearts broken just like the rest of us. 

While we love to follow the love stories of the rich and famous, we are just as addicted to the drama when their relationships combust. From the he-said-she-said to the regrets of past marriages, there are endless amounts of tabloid gossip when it comes to celebrities' love lives. Though they may move on and find love again with new partners, Hollywood stars are forever connected to their previous partners in the eyes of pop culture. Whether it was infidelity that came in between celebrity marriages, or simply that they were no longer a match — we can't help but fantasize about what could have been. From wedding bells to court settlements, we're taking a trip down memory lane and breaking down all the celebs who have regrets about getting a divorce.

Jennifer Garner and Ben Affleck were a Hollywood power couple for over a decade. The two actors originally crossed paths while starring in the 2001 film "Pearl Harbor" but it was their lead roles in "Daredevil" in 2003 that sparked a romantic relationship. In 2005 they tied the knot and went on to have three children together. Their relationship had its ups and downs, with Affleck's complicated family history taking a toll on him. He opened up to the New York Times in 2021 about his alcoholism, which landed him in rehab in 2001 and 2017. "It took me a long time to fundamentally, deeply, without a hint of doubt, admit to myself that I am an alcoholic," he admitted. 

Garner and Affleck filed for divorce in 2015. The "Suicide Squad" actor admitted on the Howard Stern Show that he and Garner drifted apart. In an interview with the Hollywood Reporter in 2021 Garner said that she's gone on to have a healthy relationship with her ex-husband. "When our kids get married, we'll dance, I know that now," she said. "We'll boogaloo and have a great time. I don't worry about that anymore."

Despite finding love again with Jennifer Lopez, Affleck admitted to the New York Times that "The biggest regret of my life is this divorce." The actor revealed he struggled to deal with the shame of failing in his marriage, adding, "But you've got to pick yourself up, learn from it, learn some more, try to move forward."

Before Will Smith found love with Jada Pinkett Smith, he was married to Sheree Zampino. The two actors met in 1991 on the set of "A Different World" through a mutual friend. On an episode of Red Table Talk, Will admitted "...I went to 'Different World' to meet Jada, and met Sheree and ended up marrying Sheree and having [my son] Trey with Sheree." The two got married in 1992 and welcomed their son the same year. 

Will and Zampino called it quits in 1995. The "I Am Legend" star admitted in a 1998 interview with Rolling Stone that after being cheated on in the past his first marriage failed largely because he "didn't trust women." In a full circle moment, Will eventually did get set up with Jada. The two started seeing each other in 1995 and wed two years later. Though they have had their ups and downs, even splitting up briefly in 2015, the two have gone on to support each other in their marriage for over two decades. 

Despite finding happiness with Jada, Will admitted to his wife on Red Table Talk that he struggled with his divorce from Zampino. "With Sheree and with Trey, that was a really difficult time. Divorce was the worst thing in my adult life, divorce was the ultimate failure for me," Smith said. Despite his past, Will has gone on to have a great relationship with his ex-wife. "Happy Bday, @shereezampino. #BestBabyMamaEver! :-) I Love You, Ree-Ree," he wrote in an Instagram post in 2018.

Before the Jenner-Kardashian clan took over with their hit show "Keeping Up with the Kardashians," Kris Jenner was a housewife with little of her own money to her name. She met her first husband, the late Robert Kardashian, in 1973 after crossing paths at a horse race. Kardashian was a powerhouse attorney, who famously represented O.J. Simpson when he was acquitted of murdering his ex-wife Nicole Brown Simpson. The two tied the knot in 1978 and went on to have four children. 

Insider sources revealed in the book "The Kardashians: An American Drama" (per PageSix) that Jenner and Kardashian lived an opulent life. Jenner was allegedly a natural host, using their former Beverly Hills mansion as the backdrop for several high-profile parties. Behind the scenes, however, Jenner's marriage to Kardashian was on the rocks. The business mogul admitted in her memoir "Kris Jenner... and All Things Kardashian,"(per Mirror) that she had an affair. "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," she admitted.

Jenner and Kardashian divorced in 1991, and the attorney passed away in 2003 after battling cancer. In an interview with OBJECTified, Jenner admitted her affair was a huge reason behind her split with Kardashian. "When I look back on it now, probably one of my biggest regrets in my life is that that marriage fell apart," she said.

Khloe Kardashian and Lamar Odom had a whirlwind romance. The two met in 2009 at a party for a mutual friend and quickly shocked fans when they tied the knot just a month later. "...It was quick. I guess that just added to the speculation— 'Why can't they wait?' I didn't want to wait," Odom told Playboy (per CBS News.) The two went on to star together on their reality show "Khloé & Lamar" which debuted in 2011 and aired for two seasons. 

The two had their ups and downs throughout their marriage, with Odom admitting in an interview with "TMZ Presents: Lamar Odom: Sex, Drugs & Kardashians" (per People) that he had multiple affairs. "Behind the scenes, I put her through s—. Like, s— that y'all don't know," he said. He also admitted that he was having "full-blown relationships" while he played in the NBA. Kardashian also admitted on the Howard Stern Show in 2016 (per Us Weekly) that Odom's struggles with substance abuse took a toll on their relationship. The couple ultimately split in 2013 after the "Good American" founder filed for divorce.

Despite their rocky marriage, Kardashian and Odom have remained on good terms. The reality star was by her ex-husband's side in 2017 after he nearly died due to a drug overdose. On a 2022 episode of Celebrity Big Brother (per International The News) Cynthia Bailey told Odom his divorce "sounds like one of your biggest regrets," to which he replied, "Yes, it is."

Courtney Cox and David Arquette first met after they both starred together in the "Scream" franchise during the 90s. After co-starring in three films together, the two wed in 1999 and welcomed their daughter Coco in 2004. The couple was married for over a decade, and they were open about the highs and lows throughout their marriage. In an interview with People, Cox said she had suffered several miscarriages with Arquette.  "[We bounced] back pretty quickly. I don't say it's a walk in the park. But what are you going to do? We just try again."

In a 2010 interview for InStyle (per Huff Post), Cox admitted that she and Arquette worked on their marriage in therapy. "We're not lazy about our marriage. We have the same arguments we've had for years." The same year, the couple split briefly in a trial separation. Though they both appeared together at the "Scream 4" premiere in 2011, and Cox supported Arquette when he competed on "Dancing With The Stars", the two filed for divorce in 2012.

In a 2014 issue of More magazine (per Daily Mail), Cox admitted "In divorce you always have regrets," adding, "We were married for a long time, so it's not like we didn't try." In an interview with The Guardian in 2021, Arquette was asked, "To whom would you most like to say sorry and why?" The "Never Been Kissed" actor replied, "My daughter, Coco, because divorce is so difficult."

Robin Thicke and Paula Patton were high school sweethearts before they became husband and wife in 2005. The two welcomed their son, Julian, in 2010 and went on to have a 21-year relationship and 9-year marriage. Patton supported her husband's music career for over a decade, even being the inspiration and album art behind his record "A Beautiful World" in 2003. While he reached new heights in his career when after dropping "Blurred Lines" alongside T.I. and Pharrell Williams in 2013, his marriage had hit new lows. "My marriage to Paula was crumbling," he told People. "I started using painkillers. It was a melting pot of trouble brewing, and I was so arrogant that I thought I could handle it all." 

Patton ultimately filed for divorce in 2014, citing infidelity and substance abuse on Thicke's part. Shortly after, the singer launched a public campaign to win Patton back. He dedicated his 2014 record "Paula" to his estranged wife, pleading with her in his track "Get Her Back." In the song he sings, "I'll wait for forever for you to love me again." During a BET performance of his song "Forever Love" that same year, Thicke told the audience, "I'd like to dedicate this song to my wife, and say, 'I miss you, and I'm sorry.'"

His public pleas weren't enough, however, as Thicke eventually moved on. After his split with Patton, the "Blurred Lines" singer started dating April Love Leary, with whom is he engaged to as of the time of writing.

Wiz Khalifa and Amber Rose started seeing each other in 2011, and they weren't shy about their love for one another. Shortly after they crossed paths, the artist debuted his leading lady when they posed together for FADER magazine that same year. Rose even got the "See You Again" singer's face tattoed on her arm in a show of affection. The artist proposed to Rose in 2012, and they welcomed their son Sebastian in 2013. Just months later, the two tied the knot with their three-month-old son in attendance. 

Their marriage was short-lived, however, as sources told TMZ that Khalifa moved out of their shared home in 2014. The insiders also claim Rose filed for divorce after discovering her then-husband with another woman. The two finalized their divorce in 2016, but their love for each other remains evident. "Too much fun with my Ex hubby last night & no we didn't celebrate our divorce we celebrated our love 4 each other cuz that never goes away," Rose tweeted at the time. 

While there's no telling whether these co-parents will reconcile — there's hope. "My #ManCrushEveryday you know what it is...We went wrong somewhere and even if we never ever get back together (Even tho I pray, dream and hope we do) he will forever be the love of my life," Rose wrote in a since-deleted Instagram post (per Essence) dedicated to her ex-husband in 2020. 

One of Hollywood's most famous former couples is nonother than Kim Kardashian and Kanye West. The two first met in 2003, but it would be nearly a decade later that their relationship became romantic. They made their debut as a couple in 2012, shortly after Kardashian's second marriage with Kris Humphries ended. West even admitted in his song "Cold" that his feelings for the SKIMS founder grew when she was still with the NBA player. Lyrics to the track include: "And I'll admit, I had fell in love with Kim / Around the same time she had fell in love with him." The pair tied the knot in an Italian ceremony in 2014 and share four children together.

Ultimately their relationship fell apart — very publicly — after Kardashian filed for divorce in 2021. West proceeded to publicly plead for his wife to come back to him — even after she started a relationship with her former boyfriend Pete Davidson. During a benefit concert in 2021, the rapper changed the lyrics to his track "Runaway" to sing "I need you to run right back to me," adding, "More specifically, Kimberly."

In 2022 he admitted to his faults in a since-removed Instagram post (via Cinema Blend.) "All I think about every day is how I get my family back together and how I heal the pain that I've caused. I take accountability for my actions. New word alert: misactions. The one thing that all my successes and failures have in common is me," the rapper wrote.

Jennifer Aniston and Brad Pitt were once one of Hollywood's most fawned-over couples. The actors first met in 1994 but didn't start dating until four years later. They went public with their romance in 1999 at the Emmy Awards and tied the knot a year later. However, Aniston questioned whether Pitt was the love of her life in a 2003 interview with W magazine. "Is he the love of my life? I think you're always sort of wondering, 'Are you the love of my life?' I mean, I don't know, I've never been someone who says, 'He's the love of my life.' He's certainly a big love in my life ...," she said in the interview.

The couple split in 2005 after the "Friends" actor filed for divorce. Shortly after, Pitt started dating Angelina Jolie. Aniston opened up about their relationship in her 2005 cover story with Vanity Fair where she admitted she and Pitt remain "committed and caring friends with great love and admiration for one another." If she could go back and change things about the relationship Aniston said: "There's a lot I would probably do differently." She went on to add, "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."