Kristin Cavallari & Jay Cutler
Though they had a happy ending as a family of five, Kristin Cavallari was the first to confess that her marriage to husband Jay Cutler was far from perfect. In July 2011, the former reality star called off their engagement, but in November of the same year, she reconnected with the Chicago Bears quarterback and announced she was expecting a child. They married in June 2013, ten months after their son Camden Jack was born.
After ten years of marriage, reality star Kristin Cavallari and NFL quarterback Jay Cutler are separating. “We have come to a loving resolution to obtain a divorce after ten years together,” the former couple announced in a joint statement released by their lawyers on social media at the time. “We have nothing but love and respect for one another and are grateful for the years we’ve spent together, the memories we’ve built, and the children we’ve raised, but unfortunately, it is simply a case of two people drifting apart. As we traverse this terrible period in our family, we ask that everyone respect our privacy.”
Kimora Lee & Russell Simmons
Russell Simmons has confessed to being a ladies’ man back in the day. He’s walked around with hundreds of stunning women on his arm over the years, the majority of whom are supermodels or actresses. However, there was only one Mrs. Simmons in his life: Kimora Lee Simmons. Russell and Kimora were the embodiments of style, celebrity, and diversity. The actor’s already popular brand investment became widely known by their collaboration and fused hip hop and high fashion. He claims he started dating Kimora shortly before her 18th birthday, eventually getting married in 1998 but separated eight years after.
Despite their failed marriage, the two stayed close friends and co-parents. Russell is now the godfather of Kimora’s two sons from previous marriages. Following his split from her former wife, he continued to date supermodels. As for Kimora, she had three more kids with Djimon Hounsou and her current husband, Tim Leissner. Russell has also starred in music videos and video games, and she was in high demand for big-screen roles.
Kelly Clarkson & Brandon Blackstock
Kelly Clarkson met her music manager husband, Brandon Blackstock, four years after she rose to prominence from American Idol. The happy couple married and have two children, and everything seemed to be going great for the couple. However, the couple has called it quits on their relationship after seven years. It’s been reported that the separation is becoming a little tumultuous.
Despite calling the turbulent year a “dumpster fire” and an “emotional rollercoaster,” Kelly revealed she took some positives from 2020, including her personal development. The American Idol alum returned to her red coaches chair on the newest season of The Voice, and the former couple’s Tennessee and California investment properties are currently for sale. There’s no news about who will own the Montana ranch, but Clarkson’s estranged husband has some sharp cowboy skills from his time in Wyoming. Although Kelly and Brandon filed for separation after seven years of marriage, their love story is one of music industry magic.
Katie Holmes & Tom Cruise
Katie Holmes and Tom Cruise’s story is one of romance, mystery, rumor—in a league of its own, to be sure. Consider yourself a typical young girl next door with a crush on Cruise. You fantasize about marrying him one day, and then, all of a sudden, you’re famous yourself, and your Cruise dream comes true. While it doesn’t seem likely, this was the truth that shaped the former couple’s relationship. They were in love in 2005, and the rest, as they claim, is history–especially now that their relationship is history.
Katie began the beautiful and satisfying journey of reinventing herself after her split, starting over in an investment home in New York with her daughter as her priority. As for Tom, given his secrecy, it’s likely that he’s in touch and shares some connection with his daughter, Suri. The actor has been collaborating with Hayley Atwell on the new Mission: Impossible film.
Denise Richards & Charlie Sheen
Before she departed from The Real Housewives of Beverly Hills, Denise Richards shared her married life with her husband Aaron Phypers on the show. Many viewers, however, recall her turbulent marriage to actor Charlie Sheen. Denise made a degree for herself as an actress before entering the reality TV scene, and she was also known as the other half of Charlie, exchanging vows back in June 2002, making their relationship official. Denise also guest-starred as Charlie’s ex in a few episodes of Two And A Half Men. On the other hand, Denise filed for a separation the following year while she was six months pregnant with their second child, Lola.
They have since been able to co-parent happily for the sake of their two children though child support problems remain. Denise’s love life took a turn for the better when she began dating Aaron. Charlie has been through a lot in his nearly 56 years and has mostly remained under the radar. He seems to look refined and is said to be dating model Julia Stambler.
Kate Hudson & Chris Robinson
Kate Hudson has been in a degree of high-profile relationships throughout the years, but she has only married once. From 2000 to 2007, the Almost Famous actress was married to Chris Robinson of The Black Crowes. Though their love story did not last, they separated after seven years of marriage and decided to share custody of their son, Ryder.
Kate and Robinson’s concentration and priority have always been on their son Ryder since their 2007 split, committing to joint custody of their son and seemed to have a good handle on co-parenting. As for their personal lives, Kate has never given up on finding her true love, and it appears that she has seen him in her boyfriend, Danny Fujikawa. They’ve traveled the world together since then and welcomed a boy. On the other hand, Chris got married to Allison Bridges and welcomed their first child, Cheyenne Genevieve.
Kaley Cuoco & Ryan Sweeting
Kaley Cuoco has had her fair share of highs and lows throughout her life, unlike her happy-go-lucky role Penny from The Big Bang Theory. She found a degree of success in acting after a brief amateur tennis career. Her love life, despite her professional success, was not always so good. The actress had been down the aisle already when she married tennis player Ryan Sweeting in a private ceremony in 2013. She claimed after the wedding that Sweeting was “the one.” However, the couple called it quits in 2015.
Cuoco has been outspoken about what contributed to their breakup, although Sweeting has maintained a low profile since the split. Despite her challenging first marriage, Cuoco finally found a new partner in Karl Cook. Moreover, her ambitions don’t end in acting as she also runs her own production company, Norman Productions, which she named after her pit bull. From what we see, Cuoco’s personal life is now on the upswing.
Jennifer Lopez & Marc Anthony
When Jennifer Lopez met Marc Anthony in 1998, she was fresh off her breakout role in the biopic Selena. They met backstage at a Broadway show and quickly became friends and partners, only to reconnect with Anthony after the breakup of her relationship with Affleck. The timing seemed to be finally perfect, and they both tied the knot in a surprise wedding at Lopez’s Beverly Hills home in a true fairy-tale style.
Lopez had a successful year in 2011. Her marriage, on the other hand, was falling apart behind the scenes. After seven years of marriage, the couple declared their separation in July 2011 to the surprise and sadness of both their fans. These days, they’re the sweetest of chart-topping ex-spouses, popping up in each other’s social media pages with their kids and giving into their fans’ chants of “Kiss! Kiss!” during award shows. Anthony and Lopez have gone onto new partnerships, new music, and new business investments in the years after their breakup. However, one can never deny the love between the former couple.
Jennifer Grey & Clark Gregg
As the new millennium unfolded, Jennifer Grey started dating Clark Gregg, tying the knot the following summer on Martha’s Vineyard, and their child, Stella, was born only five months later. The two celebrities found a way to merge their love of acting and their friendship by co-starring in the 2006 Lifetime film The Road to Christmas. Sadly, Gregg and Grey revealed their separation in a joint statement on Instagram after being together for two decades.
Grey has had successful acting career investments, but she will always be known as “Baby” from the romantic comedy Dirty Dancing. More recently, Lionsgate CEO Jon Feltheimer plans on a new Dirty Dancing film, where Grey will work as an executive producer and a lead. Meanwhile, Gregg’s tenure in the MCU came to an end — at least for the time being. Although there’s always space for Agent Coulson to return to the big screen, it doesn’t sound like there will be potential appearances anytime soon.
Jennifer Garner & Ben Affleck
Ben Affleck is no newcomer to high-profile Hollywood romances. Although the majority of his marriages haven’t ended happily ever after, the two-time Academy Award-winner hasn’t broken ties with any of his ex-girlfriends. Ben recently made headlines when fans saw him hanging out with his ex-fiancée Jennifer Lopez. Of course, let us not fail to look back on her relationship with another Jennifer, Garner.
It all started with films Pearl Harbor and Daredevil, where Ben co-starred with Garner. Ben proposed to Jennifer in 2005, and they eventually got married in June of that year. Sadly, the couple declared their split in 2015, just days after their tenth wedding anniversary. Break up is never simple, mainly when it occurs in the eyes of the general public. Despite this, Garner and Affleck have worked hard to ensure that they are good co-parents to their three children with a degree of respect towards each other.