Sean Penn's Relationship With Ex-Wife, Madonna, Married Within Six Months, Filed For Divorce Twice

Sean Penn is one of the most beloved actors and filmmakers in Hollywood. He made his debut back in the ‘70s when he appeared in a small role in the hit television series, Little House on the Prairie. He started his film career with the 1981 action drama, Taps. Following this, he landed a number of leading-man roles, which permanently solidified his footing in the film industry. Some of Sean's most notable works include State of Grace (1990), Dead Man Walking (1995), She's So Lovely (1997), All The King's Men (2006), and more. After finding huge success on the big screen, Sean Penn returned to television and has continued to do so in recent years.  

It is worth noting that during his time in the industry, Sean Penn's private life has also experienced its fair share of highs and lows, similar to his acting career. At the moment, his dating life has been creating significant buzz after he and his girlfriend, Veleria Nicov, who is 35 years younger than him, were spotted outside shopping in Santa Monica, California on January 14, 2026. However, before dating her, Sean had three marriages with high-profile women, including one with singer-songwriter, Madonna. If you are interested in knowing more about their relationship, keep on reading! 

Sean Penn and Madonna tied the knot just six months after their first meet 

According to reports, Madonna and Sean Penn first met when the actor played a small part in her music video, Material Girl, which was released in 1985. Two years later, during a casual conversation with Cosmopolitan in 1987, Madonna confessed that she knew he was ‘The One' for her from the very first moment that she laid eyes on Sean. This led her to make the first move by striking up a conversation with him on set. To top it off, after filming the MV was complete, Madonna presented flowers to everyone involved in the making of the video, but she chose to hand-deliver a rose to Sean Penn.  

Eventually, Madonna and Sean started dating, and after six months from when they first met, the couple decided to get married. Speaking to Interview Magazine, Madonna revealed she had a strong feeling that Sean was about to propose to her after seeing a “look in his eye.” In August 1985, Madonna and Sean officially tied the knot in an intimate but star-studded ceremony.  

Sean Penn's jealousy allegedly strained his marriage with Madonna  

As per reports, Sean Penn was a jealous partner. His growing jelousy became one of the major reasons why he faced a battery count for allegedly physically as**ulting David Wolonski. At the time, Sean had believed that David tried to kiss his wife, Madonna and in a fit of anger, reportedly struck him in the face and kicked him. Later, a source close to the couple revealed to People: 

“The marriage has been undergoing stress all the time, but this was the first major stress, the first really traumatic episode for her [Madonna].”  

Madonna filed for divorce from her then-husband, Sean Penn, more than once 

Although Madonna and Sean Penn seemed poised to become Hollywood's new power couple, their fans were shocked when the legendary singer decided to end her marriage in 1987. Following her divorce filing, rumours about what caused their split became the talk of the town. In an effort to offer some clarity, a representative for Madonna said: 

"There was no one direct incident leading up to this. It was a series of cumulative pressures. There were many moments in their marriage when it was shaky, and Madonna was finally forced to face the reality of the situation — that they weren't happy together."  

However, in an even more surprising move, Madonna withdrew her divorce filing just a fortnight later. While everyone thought that would be the end of it, the singer filed for divorce a second time in 1989. A few weeks later, both she and Sean signed off on the divorce papers, although a spokesperson for the actor claimed to the New York Times that their split was “amicable”.  

Following his divorce from Madonna, Sean Penn married Robin Wright and then Leila George for the third time.  

Also read: Meet Valeria Nicov, All About Sean Penn's Girlfriend With An Age Gap Of 35 Years

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