Sean Penn Scared to Date Again After 3 Failed Marriages: Women ‘Let Him Down’

Sean Penn may be bragging about being single but it’s a wall he’s put up to safeguard his feelings. He misses having romance in his life, as he never imagined growing old alone, a source tells Closer exclusively.

“He’s putting on this bravado that he’s loving the single life and doing what he wants when he wants, but no one believes him and it’s annoying to hear again and again. Surely this is just a front and coping mechanism,” the insider says.

“All the important women in his life – Elizabeth McGovern, Madonna, Robin Wright, Leila George and let’s not forget Charlize Theron – all let him down, from his warped perspective,” the source explains.

“Sean loved those date nights and would ask girls out, but the truth is he’s not the sort of guy fathers and mothers want their daughters to date. It makes him feel better to say he’s happier being single. He’s hung up about it, but everyone around knows it’s a sign of low self-esteem and insecurity and he’s just trying to validate himself,” the insider adds.

The Flag Day star, 64, told the New York Times in a June 22 profile how he was “thrilled every day” to be single.

“I’m just free. If I’m going to be in a relationship, I’m still going to be free, or I’m not going to be in it, and I’m not going to be hurting,” Sean told the publication. “I don’t sense I’ll have my heart broken by romance again.”

When recalling past relationships, the Oscar winner explained, “The first thing I see in the morning are eyes wondering what I’m going to do to make them happy that day. Rarely reciprocated.”

“On one of my marriages, the background noise of life was the [Real] Housewives of Beverly Hills or another thing called Love Island,” Sean told the Times.

He continued, “Not even being in the room — I’m not saying this to be cute — I was dying. I felt my heart, my brain shrinking. It was an assault.”

Sean has been married three times. He was wed to pop superstar Madonna, 65, from 1985 through 1989. He tied the knot with actress Robin Wright in 1996, before splitting in 2010. The duo shares two adult children: daughter Dylan Frances, 33, and Hopper Jack, 30.

The Mystic River star’s most recent marriage was to Australian actress Leila George, 32. The pair began dating in 2016 and wed in 2020. She filed for divorce in October 2021 after just over one year of marriage, citing “irreconcilable differences.”

Sean had a high-profile and PDA-filled relationship with fellow actress Charlize Theron, 48, from 2013 through 2015. After news of their split broke, rumors spread that the Mad Max: Fury Road actress ghosted her ex.

“There is a need to sensationalize things,” Charlize told WSJ magazine in March 2016. “When you leave a relationship there has to be some f–king crazy story or some crazy drama. And the f–king ghosting thing, like literally, I still don’t even know what it is. It’s just its own beast.”

“We were in a relationship and then it didn’t work anymore. And we both decided to separate. That’s it,” she said of how their split was much less dramatic than originally reported.

Sean’s most recent romance was with actress Olga Korotyayeva. They began dating in June 2023, but split after five months together.