Jennifer Lopez, Kaley Cuoco & More Celebrities

Fairytales often tell us that the perfect love story involves a charming meeting, a romantic engagement, and a picturesque wedding, followed by a happily-ever-after. However, reality doesn’t always align with these fantasies. Celebrities such as Julia Roberts and Brad Pitt are proof that love can be complicated and often ends in heartbreak, despite multiple engagements. Let’s delve into the love lives of celebrities who have been engaged three times or more, including Jennifer Lopez and Kaley Cuoco.

Kaley Cuoco, known for her role in “The Flight Attendant,” recently announced her engagement to Tom Pelphrey, making it her fourth engagement. Her first fiancé was addiction specialist Josh Resnik, who proposed in 2011, but their relationship ended in 2012. Kaley then dated tennis player Ryan Sweeting, who proposed in September 2013 after just three months of dating. They married in December 2013 but split in 2015. Kaley’s third engagement was to equestrian Karl Cook, who proposed on her birthday in December 2017. They married in 2018, but sadly separated in 2021.

Brad Pitt has also had his share of high-profile relationships. Before becoming famous, he was engaged to actress Jill Schoelen, who ended their relationship while filming a movie. Brad’s relationship with Gwyneth Paltrow made headlines when the two got engaged in 1997, only to end their engagement six months later. His next engagement was to Jennifer Aniston in 1999, and they married in 2000. Their five-year marriage ended in 2005. Brad famously fell in love with Angelina Jolie on the set of “Mr. & Mrs. Smith,” but they only got engaged in 2012. They married in 2014 and split in 2016.

Jennifer Lopez has walked down the aisle multiple times, beginning with waiter-turned-restaurateur Ojani Noa in 1997. They divorced less than a year later. JLo then married backup dancer Cris Judd in 2001, but they split after nine months. Her third marriage was to singer Marc Anthony in 2004, which ended in 2014. JLo was engaged to Alex Rodriguez in 2019, but they called it off in 2021. Interestingly, JLo and Ben Affleck rekindled their romance and got engaged again in 2022, nearly 20 years after their first engagement in 2002. They married later that year but split in 2024.

Elizabeth Taylor was engaged ten times and married eight. In 1949, William Pawley Jr. proposed, but they split before the wedding. She married Conrad Hilton Jr. in 1950 and divorced him in 1951. Elizabeth had subsequent marriages to Michael Wilding, Mike Todd, Eddie Fisher, and famously, Richard Burton, whom she married twice. Her marriages to John Warner, Larry Fortensky, and brief engagements to Victor Luna and Dennis Stein, illustrate her tumultuous love life.

Julia Roberts had three engagements before marrying Daniel Moder. She was first engaged to Dylan McDermott, followed by Kiefer Sutherland, with whom she split days before their planned wedding in 1991. In 1993, she married Lyle Lovett after a brief romance, but their marriage ended two years later.

Paris Hilton has had her share of engagements as well. She was engaged to model Jason Shaw when she was 20, but they split before marrying. In 2004, Paris got engaged to Greek shipping heir Paris Latsis but called it off in 2005. Her next engagement was to actor Chris Zylka in 2018, which ended that same year. She eventually married Carter Reum in 2021 after dating him for two years.

Kim Kardashian’s love life has also been closely followed. She was first married to producer Damon Thomas at 19, but they divorced after four years in 2004. Kris Humphries proposed to her in 2011, and they married later that year, only for Kim to file for divorce after just 72 days. Her longest marriage was to Kanye West, who proposed in 2013. They married in 2014 and divorced in 2022.

Kate Hudson has also been engaged three times. She married Chris Robinson in 2000 after just a few months of dating. Their marriage lasted seven years. She then got engaged to Matt Bellamy in 2011, but they split in 2014. Her current fiancé, Danny Fujikawa, proposed in 2021 after being friends and later dating for several years.

Drew Barrymore’s first engagement was at 16 to Leland Hayward III. She then got engaged to Jamie Walters in 1992, but they broke up in 1993. Her marriage to Jeremy Thomas in 1994 ended in less than a month. Drew’s marriage to Tom Green lasted a year, from 2001 to 2002. Her most recent marriage was to Will Kopelman, with whom she has two children. They married in 2012 and divorced in 2016.

Johnny Depp has also had five engagements but only two marriages. His first wife was Lori Anne Allison, whom he married in 1983 and divorced two years later. He was engaged to Jennifer Grey and Winona Ryder, but neither led to marriage. He married Amber Heard in 2015, but they split in 2016 amid significant legal battles.

While these celebrities have had multiple engagements, each story underscores that love is complex and unpredictable, often far different from the fairytale endings we imagine.

Source: Various sources