How long do you need to really get to know someone? Charlize Theron, 38, has finally opened up about her May-December relationship with actor Sean Penn, 53, and it turns out that this celebrity couple’s love story was almost two decades in the making.

Theron and Penn started dating seriously in February 2014 and their 15-year age difference was hardly an issue, because they were good friends for 18 years before they ever became romantically involved—an intimate May-December relationship was never something either of them saw coming.

“We had to think about it. But at the end of the day, it was somewhat effortless,” Charlize Theron recently told Vogue about her May-December relationship with Sean Penn. “It just kind of naturally happened, and before I knew it, I was in something that was making my life better—the people who really love me can see the effect it has had on me.”


Despite knowing each other in and out, and even with the age difference, the celebrity couple still faced a big hurdle—agreeing to risk their friendship for a May-December relationship that may or may not work out. “If you have that kind of enduring friendship like we did, you value it and you don’t want to just make an impulsive decision that can damage that,” the actress recently said in an interview for The Today Show. “You always kind of have to evaluate or re-evaluate your actions moving forward.”

It seems like Charlize Theron and Sean Penn made the right decision; the friends-turned-lovers look very happy together when they’re seen together, and Penn has even been seen spending quality time with Theron’s adopted two-year-old son. However, in spite of all the rumors that the celebrity couple was headed for marriage, Charlize Theron hinted that they aren’t planning to rush into anything—after all, it took the celebrity couple 18 years to realize they were perfect for each other. “I just think you should have a conscious thought process behind [going into a relationship] for sure. You can’t just willy-nilly it.”

What do you think: Would you consider dating a man you’ve been friends with for 18 years, or would you value your friendship too much to take the risk?


Harrison, L. “Charlize Theron Reveals What Might Happen If She Ever Breaks Up With Sean Penn—Watch Now!” E! News web site, May 20, 2014;


Takeda, A., “Charlize Theron Poses in a Bikini, Opens Up About Her Romance With Sean Penn: It Was ‘Effortless,’” Us Weekly web site, May 19, 2014;

Photo Credit: Everett Collection / (Charlize Theron), cinemafestival / (Sean Penn) 

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