Inside Sean Penn's History Of Age-Gap Relationships

As you might expect from an Academy Award-winning actor, Sean Penn's dating history is primarily made up of fellow A-list celebrities. However, much like his "Battle of Baktan Cross" co-star Leonardo DiCaprio — who has his own fair share of scandalous age-gap relationships — Penn has frequently made headlines for the fact that most of his romances seem to be with women who are considerably younger than him. This trend can be traced back to the 1990s, when the actor briefly dated singer Jewel, who is 14 years his junior. In 2011, Penn had a fling with Scarlett Johansson, who is 24 years younger than him, though their romance fizzled out after just a few months. 

Not long after, the "Milk" star started what would become a two-year relationship with Charlize Theron, who is 15 years younger than Penn.  Then, in 2020, the Oscar winner tied the knot with Australian actor Leila George, which marked his third marriage overall. Not only is Penn around 32 years older than George, but he's actually peers with her parents — fellow famous actors Vincent D'Onofrio and Greta Scacchi. Penn is actually the same age as her mom, and only one year younger than her dad.

Penn and George divorced in 2022, and he began seeing Ukrainian actor Olga Korotyayeva, who is about 20 years his junior, the following year. They dated for just a few months, and Penn subsequently entered a relationship with model Valeria Nicov, who is a whopping 34 years younger than him, thus marking his biggest known age-gap relationship to date.

To be fair to Sean Penn, not all of his relationships have had significant age gaps — nor has he even always been the older person in them. In fact, the "Mystic River" star's first marriage was to none other than pop sensation Madonna, who is notably two years older than him. Penn and Madonna have a complicated history, to say the very least, and their tumultuous union lasted only four years — from 1985 to 1989. An unauthorized 1991 biography of Madonna even claimed that Penn had been physically abusive during their marriage, though both Penn and Madonna herself have vehemently denied these claims.

Turning back the clock a bit, the Oscar winner also planned to marry his "Racing with the Moon" co-star Elizabeth McGovern, who is just one year younger than him. McGovern recalled their lengthy, on-again-off-again romance in a 2010 interview with the Daily Mail. Penn's former fiancée confessed that she "didn't want to get married, but [Penn] did — or at least he said he did." The "Downton Abbey" star went on to confirm that she ultimately broke things off upon realizing that their lifestyles simply weren't compatible. 

Years later, in 1996, Penn tied the knot with "Forrest Gump" star Robin Wright, who is about six years younger than him. The celebrity couple called it quits in 2010 after 14 years of marriage, though not before they had two children, Dylan and Hopper Penn. The A-listers are on good terms nowadays, though it admittedly took them a while to get there.