Charlize Theron & Sean Penn Relationship Timeline — PICS

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June 17, 2015 3:55PM EDT

Sean Penn and Charlize Theron were one of Hollywood’s hottest couples at one point in time. Relive their romance with these pics.

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Sean Penn and Charlize Theron at the Aids Solidarity Gala at the Life Ball

Sean Penn and Charlize Theron at the Aids Solidarity Gala at the Life Ball — Sean Penn and Charlize Theron were an understated power couple when they were together in the mid-2010s. The two Oscar winners started dating in December 2013 and were put under a microscope by the press due to their age difference, with Sean being 15 years her senior. The two kept a low profile, however. They merely stepped out for major industry events and film premieres.

The two were going strong for well over a year, but by June 2015, Charlize decided to end the relationship. They did work together, though. Sean directed Charlize in his 2016 film ‘The Last Face,’ which premiered at the Cannes Film Festival almost one year after the two split.

Here, Sean Penn and Charlize Theron pose for photos at the Aids Solidarity Gala at the Life Ball in Vienna on May 16, 2015. To see more images of Sean and Charlize together during their relationship, take a look through the rest of the gallery by scrolling through the photos below!

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Charlize Theron and Sean Penn at the Warner Bros. Premiere of ‘Mad Max: Fury Road’

Charlize Theron and Sean Penn at the Warner Bros. Premiere of ‘Mad Max: Fury Road’ — Charlize Theron and Sean Penn seen at the Warner Bros. premiere of ‘Mad Max: Fury Road’ in Los Angeles. The two were still going strong by this point, having celebrated over one year together.

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Charlize Theron and Sean Penn at the Life Ball

Charlize Theron and Sean Penn at the Life Ball — Charlize Theron and Sean Penn at the Life Ball in Vienna on May 16, 2015. Things seemed to be going well for Sean and Charlize during this time in their relationship. Unfortunatley, the two wouldn’t be together for much longer, with Charlize making the ultimate decision to end their romance one month later.

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Charlize Theron and Sean Penn at the ‘Mad Max: Fury Road’ premiere

Charlize Theron and Sean Penn at the ‘Mad Max: Fury Road’ premiere — Charlize Theron and Sean Penn at the ‘Mad Max: Fury Road’ premiere at the 68th Cannes Film Festival on May 14, 2015. The photo was taken just one month before Charlize made the decision to end her relationship with Sean.

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Sean Penn and Charlize Theron at ‘The Last Face’ premiere

Sean Penn and Charlize Theron at ‘The Last Face’ premiere — Sean Penn and Charlize Theron at ‘The Last Face’ premiere at the 69th Cannes Film Festival on May 20, 2016. The two had nearly been broken up for almost a year at this point, but chose to keep things incredibly congenial at major events.

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