15 Stars Who Dated/Married Younger People and Regretted It

This is 2017, and we are way past the time when we can judge a couple’s age gap, and it should not really matter if someone is dating a woman 20 years his junior, as long as they are compatible. But Hollywood is messy and gets unpredictable with each passing day. Dating a person who is substantially younger might end up being a lot of work. In these stars’ cases, at least, things went down south pretty fast, when they ignored the age tag.

1Tom Cruise

Possibly the murkiest divorces of the decade. When Tom Cruise fell in love with Katie holmes, he jumped up and down on Oprah Winfrey’s couch. Katie was 16 years younger than the twice-divorced Tom, and yet they were incredibly happy for quite some time. They got married and had their daughter Suri, but their marriage only lasted six years. Tom had a relentless spiritual obsession with the cult of Scientology, and wanted to pursue their lifestyle.

Katie was of course a lot more liberal and never wanted her daughter to grow up under religious pressures. While, some say Scientology split them up, their huge age gap could not have possibly helped, especially since Katie did give up work for a while, while she was married.

Tom Cruise

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2 Bradley Cooper

When 40-something Bradley Cooper started seeing British model Suki Waterhouse in 2011, people thought it could never get serious. Suki was 17 years Bradley’s junior and did not even share the same countries. But despite all odds, Bradley and Sui did manage to sustain the relationship for two years. Until 2013, when they broke up, and it was reported that their huge age difference is the reason behind the split. Also, Suki wanted to focus on her career, which led to them spending a lot of time apart, which obviously didn’t help.

Bradley Cooper

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3 Leonardo DiCaprio

Leo is known for dating younger women, almost exclusively. From Blake Lively to supermodel Toni Garrn, Leonardo has dated a string of younger women. But one his longest relationship was with Sports Illustrated model Nina Agdal. Nina, who is just 25, met the 42-year-old Leonardo through friends and embarked on a year-long relationship together. Though they never made any red carpet appearances, they were seen hanging out and vacationing together multiple times.

They broke up last year, and though they continue to remain friends, Leo’s friends insist that they split up as they were just not compatible and the age gap was too big for them to have something in common.

Leonardo DiCaprio

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4 Johnny Depp

The divorce that shocked Hollywood – when Johnny Depp started dating actor Amber Heard, who was 23 years younger than him, his friends including Angelina Jolie, called it a mid-life crisis. Nobody thought Johnny and Amber would made it work, especially since Johnny was just getting out of a 14-year-old relationship with supermodel Vanessa Pardis. They eventually married in 2014, and started having problems within a year.

Amber filed for divorce 15 months after their marriage and accused Johnny of physical and mental abuse. The divorce proceedings took an ugly turn, and now Johnny Depp’s Hollywood career is at stake. Most of his fans are alienated from him seeing the charges against him and have vowed to never see his movies.

Johnny Depp

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5 Demi Moore

Twice-divorced Demi Moore stunned Hollywood when she chose to marry a 15-years younger Ashton Kutcher in 2003. Demi was a Hollywood icon, whereas Ashton was just hitting his stride. Their marriage lasted eight years, but came to an end in 2011, when Demi filed for divorce citing ‘irreconcilable differences.; Friends close to the couple still believe that though Ashton was quite close to all of Demi’s children, the couple’s age gap became the bigger issue.

Demi Moore

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6 Jennifer Lopez

Jennifer Lopez’s friends had warned her against getting serious with her back-up dancer Casper Smart, as they thought it could never be more than a fling. Moreover, Casper was 18 years younger than J-Lo, and their relationship was famously unstable. For five years, the couple had an on-again-off-again thing, and even their friends stopped keeping tabs on their relationship. They finally broke it off in 2016.

Jennifer Lopez

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7 Angelina Jolie and Billy Bob Thornton

The couple had an erratic relationship which often shocked Hollywood. Billy was exactly 20 years older than Angelina, and she was just finding fame in showbiz. Angelina famously wore Billy’s blood in a vial on her neck at an Oscars red carpet, but the duo’s marriage did not find stability. They married only after a two-month courtship, and eventually found out that they did not have much in common, Billy even said that Angelina’s lifestyle was too much for him to handle.

Angelina Jolie and Billy Bob Thornton

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8 Madonna

Madonna dated Jesus Luz, who was 28-years-younger to her. The relationship was very erratic and Luz broke up with the 51-year-old Madonna as they had nothing in common. A source for Madonna commented that the couple are still friends.

Madonna dated Jesus Luz

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9 Kate Hudson

Kate Hudson hooked up with dancer Derek Hough after calling off her three-year long engagement to Muse frontman Matt Bellamy. This shocked Hollywood, and even Kate’s family as Kate has a son with Matt, and the two were going pretty strong. Nevertheless, Derek and Kate’s relationship did not last as the two are years apart.

Kate Hudson

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10 Tom Hiddleston

Tom Hiddleston’s fans could not believe that the actor would ever date Taylor Swift who was not just 10 years younger to him, but also had a huge reputation for publicizing her personal life. Tom has been a private person, but his fling with Taylor brought his life under scrutiny. The duo were only together for 3 months, and had a whirlwind romance. After their break-up Tom had admitted that the media attention was too much and their relationship had run its course.

Tom Hiddleston

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11 Robin Wright

In 2012, House of Cards star Robin Wright started dating actor Ben Foster who was 14 years younger to her. After going strong for two years, announced their engagement. But things took a turn for the worse in the next few months and the couple split in 2014. But they again reconciled briefly for a few months, but realized that the age gap was too much and broke up again in 2015.

Robin Wright dating actor Ben Foster

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12 Sean Penn

Sean Penn and Charlize Theron’s fans were thrilled when the two actors started dating. The couple made for a smashing power couple in spite of their 15-year age gap. They even got engaged after just a year of being together, and even worked together in a film. But things soon got rocky, and they ended their relationship in 2015. Their split came as a shock as their friends and family had thought that all’s well between the two.

Sean Penn

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13 Darren Aronofsky

Black Swan director Darren Aronofsky began dating the lead actress from his 2017 film mother, Jennifer Lawrence. The couple had a 22-year age gap and obviously could not sustain the relationship beyond a few months. The couple appeared to be very happy and chatty on their film’s premieres, but the film did not do well at the box office. Soon after the film released, they broke up. Close friends believe that the besides the huge age difference, Jennifer was not happy with how the film came out and that affected their relationship in a big way.

Darren Aronofsky

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14 Halle Berry

Halle Berry had a tumultuous relationship with Canadian model Gabriel Aubry, who was 10 years her junior. The couple had a daughter together, but they broke up after five years, and were involved in a long and tedious custody battle over their daughter. Berry and Aubry are still not on cordial terms.

Gabriel Aubry and Halle Berry

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15 Scott Disick

Reality star Scott Disick has a reputation for being a womanizer. In fact, after his break-up with longtime partner Kourtney Kardashian, he became more of a playboy and started dating 19-year-old actor Bella Thorne. Bella, too, has had a string of relationships in the past, and her fling with Scott did not last, as the couple had a 15-year age gap. But Scott never heard the end of it from the Kardashians who relentlessly went against him for dating someone so young and problematic.

Scott Disick

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