A journey through Sean Penn's romantic past: From Madonna to Charlize Theron

Sean Penn's celebrity-studded love life and interpersonal relationships have drawn media attention to his life. Penn's romantic adventures have entwined with his remarkable profession, from high-profile marriages to whispered loves.

Outlook International Desk

Updated on: 16 August 2023 3:54 pm

American actor Sean Penne

With a multi-decade career, talented American actor and filmmaker Sean Penn has captured the public's interest with his personal life and romantic interests.Throughout his life, he has been involved in several high-profile relationships and marriages. Here are some of the romantic relationships and marriages in which Sean Penn was involved:

Elizabeth McGovern

The Downton Abbey (2010-2015)star and Penn met early in their careers while co-starring in the 1984 movie Racing with the Moon. Their relationship quickly grew, leading to an engagement. According to reports, Penn proposed to McGovern when she was only 23 years old. Nevertheless, the union was just temporary and lasted for two years.

Madonna

One of Sean Penn's most famous relationships was with the pop icon Madonna. The two were married in 1985 but had a tumultuous relationship that attracted a lot of media attention. The relationship ended after only two years but the couple divorced in 1989.

Robin Wright

Following his divorce from Madonna, Sean Penn married House of Cards (2013-2018) actress Robin Wright in 1996. They had two children together, a daughter named Dylan Frances and a son named Hopper Jack. However, their marriage also faced its share of difficulties and the couple filed for divorce multiple times. They eventually finalized their divorce in 2010.

Jewel

After witnessing Jewel's debut performance on “Late Night with Conan O'Brien” in 1995, Penn made contact with her at her family's Alaskan residence to set up a meeting. They didn't last long, according to Jewel, who described the actor as "a fantastic flirt" and persistent in his pursuit of her. However, the actress knew she was leery of becoming recognised as an A-lister's girlfriend rather than known for her merits.

Scarlett Johansson

After his divorce from Robin Wright, Sean Penn was briefly linked to actress Scarlett Johansson in 2011. The relationship was never officially confirmed, but the two were spotted together on multiple occasions. One of the prominent occasions that made headlines of the pairing was the White House Correspondents dinner in May 2011.

Charlize Theron

Sean Penn and Charlize Theron began dating in late 2013 and got engaged in 2014. However, their engagement was called off in 2015, leading to the end of their relationship. The exact reasons for their breakup have not been explicitly stated by either of them.

Leila George

In 2016, Sean Penn started dating actress Leila George, daughter of actors Vincent D'Onofrio and Greta Scacchi. The couple kept their relationship relatively private and eventually got married in a private ceremony in 2020 but separated paths in 2022.