Top Women Sean Penn Has Dated

Sean Penn’s relationships have often overlapped with major chapters in his acting and directing career, from early breakout films in the 1980s to more recent projects. Over the years he has dated and married several high-profile women from film, television, and fashion, with timelines that often connect to specific productions or philanthropic work.

This list gathers notable relationships that were widely covered at the time they happened. Each entry includes clear time frames, professional context, and key facts, so you can follow how these relationships fit alongside Penn’s work and public life.

Madonna

Sean Penn and Madonna married in August 1985 in Malibu and divorced in 1989. They worked together on the film ‘Shanghai Surprise’, which was released in 1986. During their marriage Penn was continuing his rise from early roles into more prominent parts while Madonna was in the middle of a run of hit albums and tours.

Their relationship drew heavy media attention throughout the late 1980s. After their divorce both continued to appear at major industry events, and each went on to focus on new creative projects and personal milestones.

Robin Wright

Sean Penn began a relationship with Robin Wright in the early 1990s. They married in 1996 and divorced in 2010. The couple had two children during their years together, and Penn’s work as an actor and director accelerated in that period with films like ‘Dead Man Walking’ and ‘The Crossing Guard’.

Wright continued building her own career through a mix of film and later television work. The two finalized their split in 2010 and have maintained separate professional paths since, while both remaining active in film and advocacy.

Charlize Theron

Sean Penn and Charlize Theron dated from around 2013 to 2015. Theron starred in ‘The Last Face’, a film Penn directed that premiered later. Their relationship coincided with Theron’s busy schedule on large-scale productions and Penn’s continued focus on directing and humanitarian efforts.

Reports of an engagement circulated at the time, and the pair attended several public events together before separating in 2015. After the split they returned to independent projects and appearances without further collaboration.

Leila George

Sean Penn married Leila George in 2020. She is an actress who has appeared in projects such as ‘Animal Kingdom’ and is the daughter of actors Vincent D’Onofrio and Greta Scacchi. The marriage followed several years in which Penn balanced acting, directing, and philanthropic work.

George filed for divorce in 2021 and the divorce was finalized in 2022. Following the dissolution both continued to work on new roles and creative projects, and Penn returned to set on multiple productions soon after.

Elizabeth McGovern

Sean Penn dated Elizabeth McGovern after they co-starred in ‘Racing with the Moon’, which was released in 1984. Their relationship developed as both were gaining attention from early film roles and awards-season visibility.

They were briefly engaged before parting ways. McGovern continued her career on stage and screen, and Penn moved on to subsequent projects that expanded his profile in the industry.

Scarlett Johansson

Sean Penn and Scarlett Johansson were widely reported to be dating in 2011. They appeared together at several events during that period, which coincided with Johansson’s busy release slate and Penn’s ongoing charity work related to disaster relief.

The relationship lasted for a short period that year. Afterward both focused on separate film commitments and public appearances, and there were no further collaborations between them.

Petra Němcová

Sean Penn and model Petra Nemcova were linked in reports around 2008. Their connection followed high-visibility charity events, including those related to international relief efforts that Penn supported at the time.

The reported relationship lasted for a brief period. Nemcova continued her work in fashion and philanthropy, while Penn proceeded with film roles and the ongoing development of his humanitarian initiatives.

Valeria Golino

Sean Penn and Italian actress Valeria Golino were linked in the late 1980s and early 1990s. The period overlapped with roles that brought Golino to wider U.S. audiences and with Penn’s transition into directing alongside acting.

Their relationship concluded as both pursued separate film work in the United States and Europe. Golino continued acting and later directing, while Penn advanced with performances that led to major accolades.

Christina Applegate

Sean Penn was reported to have dated Christina Applegate briefly in the late 1980s. The timing aligned with Applegate’s early television success and Penn’s rising profile from a mix of dramatic and thriller roles.

The relationship did not continue beyond that period. Applegate moved forward with a long-running television career and film roles, while Penn focused on a slate of projects that added to his critical recognition.

Share your picks for Penn’s most notable relationships in the comments and tell us which ones you think defined key moments in his career.