10 Devastating Celebrity Affairs That Left Lives in Ruins

By Krystal Brown

Similar to ordinary individuals, celebrities also experience their share of relationship challenges. We examine 10 of the most destructive infidelities that wreaked havoc on people’s lives.

Marilyn Monroe and John F. Kennedy

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Rumors of an affair between Monroe and President Kennedy while he was married to Jackie Kennedy were rife in the 60s. The flames were fanned even further when Monroe seductively performed “Happy Birthday” to Kennedy at a fundraiser in Madison Square Garden. There were also rumors that Monroe had an affair with Kennedy’s brother Robert F. Kennedy.

Ryan Phillippe and Reese Witherspoon

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Hollywood sweethearts Phillipe and Witherspoon first met at Witherspoon’s 21st birthday party back in 1997 and quickly got engaged a year later. They went on to marry and have 2 children but life did not stay sweet for long. Withersppon filed for divorce in 2006 when asked for sole custody of her children after Phillipe had an affair with Stop-Loss co-star Abbie Cornish. While the couple officially said that they divorced due to irreconcilable differences there was speculation in Hollywood that Ryan cheated on his wife. 

Brad Pitt and Angelina Jolie

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Brad Pitt and Jennifer Aniston appeared to be the Hollywood marriage of dreams but their marriage did not last long when rumors started that Pitt was having an affair with his Mr & Mrs. Smith co-star Angelina Jolie. Jolie says she could not help but fall in love with Pitt and Aniston was left devastated and filed for divorce in 2005. After causing a lot of hurt and distress, Pitt and Jolie went on to end their 10-year relationship in 2016. 

Humphrey Bogart and Lauren Bacall

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Bogart and Bacall met in 1944 on the set of To Have and Have Not and despite a 25-year age gap (Bogart was 44 and Bacall 19) they started an affair. Bogart was married at the time so there was understandable gossip in Hollywood. When the film’s director Howard Hawks discovered the romance he allegedly threatened to end her career if she did not end things with Bogart as he had feelings for her himself. The relationship between the two stars continued, and they went on to get married in 1945 and had 2 children together. 

Hugh Grant and Divine Brown

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Grant was in a relationship with British actress and model Elizabeth Hurley for 13 years when Grant hit the headlines in a very controversial way. Grant was arrested on Hollywood Boulevard when he was caught with prostitute Divine Brown. Hurley forgave Grant for his misdemeanor and their relationship continued for another 5 years before it ended on amicable terms. 

Ethan Hawke and Nanny

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Ethan Hawke and Uma Thurman met on the set of Gattaca in 1997 and quickly fell in love, getting married just a year later. They had two children together and spent a few happy years together until things started to go wrong and they eventually divorced in 2005. Hawke has always denied having a relationship with the couple’s nanny Ryan Shawhughes but Hawke and Shawhughes went on to marry in 2008 and have two children together.

Kristen Stewart and Rupert Sanders

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Kristen Stewart and Robert Pattinson enjoyed being the hottest couple in town until Stweart cheated on Pattinson with her Snow White and the Huntsman director, Rupert Sanders. The 2012 affair caused heartbreak to both Pattinson and Sanders’ wife who he was still married to at the time of the affair. The couple who had the affair made public apologies but fans were not happy despite Pattinson and Sanders staying in a relationship for another year. 

David Letterman and Several Women

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The Late Show host David Letterman married his second wife Regina Lasko in 2009 after a long-term relationship. Just 6 months after the pair married Letterman admitted to having relationships with various women who worked on his show. Letterman and Lasko worked things out and are still together after he told Oprah that he was “trying to fix it.”

Tiger Woods and Several Women

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Golfer Woods hit the headlines In 2009 when it was revealed that he cheated on his wife Elin Nordegren with Rachel Uchitel, a nightclub manager. It was alleged that Nordegren attacked Woods with a golf club when she found out about the affair. 12 other women came out to say that they had an affair with Woods which led to a severe dent in his reputation that included losing endorsements, taking a break from golf, and a divorce from Nordegren.

Jesse James and Several Women

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Another serial cheater is Jesse James who famously cheated on Sandra Bullock several times. Bullock was aware that James was a bad boy when she married him in 2005 but it seemed even she could not tame him during their 5 year marriage. Bullock tried to put on a brave face when allegations came out about his affairs in 2010 but it was not to be and the couple divorced. 

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