The Oscar winner also laments he could never play a role like Harvey Milk now because straight actors playing gay is too hotly debated, calling it "a timid and artless policy toward the human imagination."

Sean Penn may be "thrilled every day" that he's a single man, but he hasn't been enjoying his career nearly as much. The Academy Award-winning actor apparently hasn't enjoyed a film set since 2008's Milk , for which he won his second Oscar.

The venerated actor talked about relationships and his career as part of a wide-ranging interview with The New York Times that was published over the weekend. In it, he opened up about the importance of personal freedom at this point in his life, and relationships.

"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," he told the Times. "I don't sense I'll have my heart broken by romance again."

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No More Drama

He expressed a bitterness about some of his previous relationships, without offering any specifics, saying that he would remember waking up and "the first thing I see in the morning are eyes wondering what I’m going to do to make them happy that day." He added that it was "rarely reciprocated."

Penn was married to Madonna from 1985 to 1989. He then was wed to Robin Wright from 1996 to 2010, sharing two children with her, Dylan Frances, 33, and Hopper Jack, 30. He then married Leila George in 2020, but that union would only last two years.

He hinted that in one of those marriages, "the background noise of life was a Real Housewives of Beverly Hills or another thing called Love Island ." He said that even when he wasn't present while these reality shows were being consumed, "I was dying. I felt my heart, my braining shrinking. It was an assault."

Now, when it comes to love and relationships, Penn is anti-drama. He credits his female friends, whom he describes as these "beautiful, wonderful people, wonderful with their partners or wonderful on their own," for teaching him that "relationships don’t have to be dramatic or draining."

Penn also weighed in on rumors about a ton of drama and trauma -- including speculation of violence -- in his marriage to Madonna. You can read all about that right here :

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Can't Play Gay

While he's finding his path to happiness in his personal life, Penn also confessed to being dissatisfied professionally. In the same interview, he admitted that "the last time I had a good time" on a film set was when he was filming Milk in 2008.

"I went 15 years miserable on sets," Penn added.

He explained what he meant by saying that it has to do with him being "a known actor" in the lead role and getting paid well, as that creates an expectation of "a leadership position on a film and you’ve got to show up with energy and be a bodyguard for the director in some way."

The actor said he was "faking" his way through that and found it "exhausting." He explained, "Mostly what I thought was just, ‘What time is it? When are we going to get off?’"

He even suggested that he'd have walked away entirely, "but I didn't know how I was going to keep my house running or travel freely or things like that if I stopped."

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That's the way things were going for him, Penn said, until Dakota Johnson sent him the screenplay for their new film Daddio . "I felt like this could be a pleasant experience and that's gonna matter to me now, maybe more than in the past," he said, adding that he did find himself enjoying the process.

That makes it the first set he's enjoyed since the aforementioned Milk , a role Penn doesn't think he'd ever be allowed to portray now. The real-life Harvey Milk was an openly gay political figure. According to Penn, the issue of straight actors playing gay characters (real or imaginary) is just too hot-button right now.

"No. It could not happen in a time like this," he said of playing a role like Harvey Milk in 2024. "It’s a time of tremendous overreach. It's a timid and artless policy toward the human imagination."

Penn and Johnson's Daddio hits theaters this Friday, June 28.

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