News These Photos of Charlize Theron and Sean Penn Hugging Post-Split Will Make You Cringe #TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time. By Isabel Jones Isabel Jones Instagram Twitter Isabel is an Oregon-born and Brooklyn-based writer and editor with a special interest in pop culture. InStyle's editorial guidelines Updated on April 18, 2019 @ 03:45PM Pin Share Tweet Email Who: South African Oscar-winning actress Charlize Theron, 43, and two-time Oscar-winning actor and director Sean Penn, 58. Ian Gavan/Getty Images How They Met: Funny enough, Charlize and Sean’s paths crossed many times through the years before they began dating in late 2013. In 2015, Theron told Esquire that she and Penn had been friends for 20 years. In 2004, they even won their first Oscars on the same night (hers for her performance in Monster, and his for Mystic River). J. Vespa/Getty Images “I think our friendship stemmed from mutual respect — more on my end, because I really didn't have a body of work twenty years ago, but my love and passion for making films — that was our common ground,” she explained. “And also, Sean liked to have conversations outside of just making movies. That's sometimes hard to find among friends here, and that's where our friendship really blossomed.” Speculation that Theron and Penn’s bond had stretched into more-than-friends territory began in early 2014 when photos of the duo celebrating the new year in Hawaii surfaced. TBT: Prince William Used to Impersonate Prince Harry's Then-Girlfriend Chelsy Davy and Make Hilarious Prank Calls Soon after their relationship was confirmed, engagement rumors began to circulate — but while Penn seemed down for marriage no. 3 (he’d previously wed Madonna and Robin Wright), telling Esquire U.K., “You say I’ve been married twice before, but I’ve been married under circumstances where I was less informed than I am today. So I wouldn’t even consider it a third marriage, I’d consider it a first marriage on its own terms if I got married again,” Theron was more apprehensive. Thomas Niedermueller/Life Ball 2/Getty Images In 2014, she told Vogue, “Let’s put it this way: I never had the dream of the white dress. And watching other people getting married? I think it’s beautiful for them, but to be quite honest, usually I’m sitting there just devastated. It’s supposed to be this night of celebrating love, and all you see is a couple separated all night making sure everybody else is OK. It just looks like a lot of work. And as you get older, you start sifting through the stuff that really matters.” TBT: The Story of Patricia Arquette and Nicolas Cage’s Relationship Is the Weirdest Thing You’ll Ever Read Why We Loved Them: There’s something comforting about seeing a statuesque woman standing next to her shorter partner. Not only does Charlize have two inches on Sean, but she never shied away from wearing heels when they were out together (though, to be fair, they did play the stair card on occasion). Dimitrios Kambouris/Getty Images When They Peaked: The best part of this relationship was probably the way they each embraced each other’s children but respected parental boundaries. Theron, who’d adopted son Jackson in 2012, made it clear that while Penn was part of her son’s life, he wasn’t about to become Daddy Sean. "There was an understanding that I was a single mom with a very young boy who I had to put in a situation where he understood that Mommy dates, but that he does not have a father,” Theron told the Wall Street Journal nearly a year after their split. "You have to be very careful and very honest about that stuff. And Sean was great with all of that.” And though they broke up before the adoption of Theron’s second child, daughter August, she and Penn had agreed to a similar arrangement: “We had a very clear understanding. He knew that I was thinking about filing for another adoption, but that we weren't filing together.” JB Lacroix/Getty Images TBT: Alanis Morissette Hit “Rock Bottom” When She and Ryan Reynolds Called Off Their Engagement Meanwhile, Penn and ex-wife Robin Wright’s daughter Dylan gushed about Theron, calling dad’s then-girlfriend “brilliant.” “She's the only woman since my mom who can shut my dad up. The only woman!” she told Us Weekly in 2014. The Breakup: By June 2015, the pair’s split was official, mere weeks after they’d made their glamorous Cannes debut. Danny E. Martindale/Getty Images There are myriad factors that may have contributed to the couple’s demise: perhaps Penn craved a larger role in Theron’s children’s lives, or Penn directing Theron in The Last Face was a catastrophic melding of business and pleasure. But what ended up being reported didn’t fit into a logical narrative at all: Charlize ghosted Sean. After the media began to run with this rumor as fact, Theron intervened, telling WSJ, “We were in a relationship and then it didn't work anymore. And we both decided to separate. That's it." "There is a need to sensationalize things. When you leave a relationship there has to be some f—ing crazy story or some crazy drama. And the f—ing ghosting thing, like literally, I still don't even know what it is. It's just its own beast." TBT: Why Does Jake Gyllenhaal Always Stare at His Girlfriends While They're Eating? A couple months later, Theron clarified the extent of her and Penn’s very healthy, communicative post-split relationship, telling GQ, "I saw him yesterday! He's still editing [The Last Face]. But people want to create chaos with celebrities, as if [when] there's not drama around it, somehow it doesn't sell." Though, to be fair, the Last Face press tour did produce some painfully awkward photos: Tristan Fewings/Getty Images George Pimentel/Getty Images Tristan Fewings/Getty Images Fast forward to 2019, and if there was ever a question as to whether Theron had gotten over Penn, that’s ancient history — in fact, she doesn’t even seem to remember that they ever dated … While promoting her new film, Long Shot, Charlize told Entertainment Tonight that she’s “shockingly available” and has been for, uh … “10 years.” Um, we beg to differ? “Somebody just needs to grow a pair and step up," she told the outlet. And yes, that seems valid. I mean, there’s really no need to fear humiliation — she probably won’t even remember rejecting you. Cameron Diaz and Alex Rodriguez Nearly Broke the Internet with This 2011 Photo Where They Are Now: Penn has a film with Mel Gibson and Natalie Dormer, The Professor and the Madman, out this May and a couple of other projects in development. On the personal front, he’s been linked to 27-year-old actress Leila George since 2016 but it’s unclear if they’re still together. As mentioned above, Charlize is “shockingly available” and hasn’t dated anyone since 2009 (except for Sean Penn for nearly two years). She was rumored to be dating Brad Pitt in January, but insiders quickly debunked that story. And though she’s apparently single af, we don’t know when she’d even find the time to date, because she’s acting and producing up a storm. Long Shot opens on May 3, she recently wrapped filming the Untitled Roger Ailes Project (in which she stars as conservative talk show host Megyn Kelly), and an Atomic Blonde 2 is in the works.