Sean Penn, 63, ‘thrilled every day’ to be single after string of failed romances with A-list stars and vows he’ll never be ‘heart broken again’

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Sean Penn is ‘thrilled every day’ to be single and has vowed to remain ‘free’ even if he gets into a relationship so that he’ll never have his ‘heart broken by romance again.’

‘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,’ the thrice-divorced 63-year-old declared to the New York Times last Saturday.

‘I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again.’

Sean stressed that ‘relationships don’t have to be dramatic or draining’ and he avoids ‘unnecessary drama and visits from “the trauma gods.”‘

In the past, Penn lamented that ‘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.’

Sean Penn is ‘thrilled every day’ to be single and has vowed to remain ‘free’ even if he gets into a relationship so that he’ll never have his ‘heart broken by romance again’ (pictured June 13)

The thrice-divorced 63-year-old declared to the New York Times last Saturday: '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. I'm not going to be hurting. I don't sense I'll have my heart broken by romance again'

The thrice-divorced 63-year-old declared to the New York Times last Saturday: ‘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. I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again’

The two-time Oscar winner – who hasn’t been pictured with girlfriend Olga Korotyayeva since October – was last spotted canoodling with Peruvian-Australian 39-year-old actress, Nathalie Kelley, in Miami last December.

Sean dated his third wife – Australian actress Leila George – for four years before officially ending their 15-month marriage in 2022.

The odds were stacked against the May-December couple considering Penn is about the same age as the 32-year-old nepo-baby’s famous father, Emmy nominee Vincent D’Onofrio.

‘On one of my marriages, the background noise of life was a [Real] Housewives of Beverly Hills or another thing called Love Island,’ groaned the Malibu native, hinting it was Leila.

‘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.’

But back in 2015, Sean revealed he loved watching ABC’s The Bachelor with then girlfriend, Charlize Theron.

‘I don’t really want to hear the conversations. I want to know the decisions. Is he gonna decide on this one or this one?’ Penn explained on Jimmy Kimmel Live!

‘And I wanna see somebody cry, and then see somebody get ecstatic and then see them cry.’

Sean stressed that 'relationships don't have to be dramatic or draining' and he avoids 'unnecessary drama and visits from "the trauma gods"'

Sean stressed that ‘relationships don’t have to be dramatic or draining’ and he avoids ‘unnecessary drama and visits from “the trauma gods”‘

In the past, Penn lamented that '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'

In the past, Penn lamented that ‘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’

The two-time Oscar winner - who hasn't been pictured with girlfriend Olga Korotyayeva since October - was last spotted canoodling with Peruvian-Australian 39-year-old actress, Nathalie Kelley (pictured June 14), in Miami last December

The two-time Oscar winner – who hasn’t been pictured with girlfriend Olga Korotyayeva since October – was last spotted canoodling with Peruvian-Australian 39-year-old actress, Nathalie Kelley (pictured June 14), in Miami last December

Sean dated his third wife - Australian actress Leila George (R, pictured in 2020) - for four years before officially ending their 15-month marriage in 2022

Sean dated his third wife – Australian actress Leila George (R, pictured in 2020) – for four years before officially ending their 15-month marriage in 2022

The odds were stacked against the May-December couple considering Penn is about the same age as the 32-year-old nepo-baby's famous father, Emmy nominee Vincent D'Onofrio (R, pictured in 2022)

The odds were stacked against the May-December couple considering Penn is about the same age as the 32-year-old nepo-baby’s famous father, Emmy nominee Vincent D’Onofrio (R, pictured in 2022)

The Malibu native groaned: 'On one of my marriages, the background noise of life was a [Real] Housewives of Beverly Hills or another thing called Love Island. 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'

The Malibu native groaned: ‘On one of my marriages, the background noise of life was a [Real] Housewives of Beverly Hills or another thing called Love Island. 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’

But back in 2015, Sean revealed he loved watching ABC's The Bachelor with then girlfriend, Charlize Theron (R, pictured in 2015)

But back in 2015, Sean revealed he loved watching ABC’s The Bachelor with then girlfriend, Charlize Theron (R, pictured in 2015)

Penn explained on Jimmy Kimmel Live! at the time: 'I don't really want to hear the conversations. I want to know the decisions. Is he gonna decide on this one or this one? And I wanna see somebody cry, and then see somebody get ecstatic and then see them cry'

Penn explained on Jimmy Kimmel Live! at the time: ‘I don’t really want to hear the conversations. I want to know the decisions. Is he gonna decide on this one or this one? And I wanna see somebody cry, and then see somebody get ecstatic and then see them cry’

The Asphalt City producer-star famously split from his second wife – eight-time Emmy nominee Robin Wright – four times during their 21-year relationship – in 1995, 2007, and twice in 2009 – before finally ending their 13-year marriage in 2010.

Sean and his 58-year-old Crossing Guard leading lady are proud parents of 33-year-old daughter Dylan Frances Penn and 30-year-old son Hopper Jack Penn, but this was a point of contention during the divorce.

By contrast, Penn remains amicable with his first wife – seven-time Grammy-winning pop diva Madonna – whom he divorced in 1989 after three years of marriage.

‘It turns out it’s a lot quicker to repair a friendship after divorce if there are not kids involved,’ the CORE co-founder noted.

‘It took Robin and I quite a while. There was a lot of drama. Much more important to repair it if there are kids involved, but no easy swing, right?’

Sean has also reportedly romanced Elizabeth McGovern, Susan Sarandon, Brigitte Nielsen, Emily Lloyd, Jewel, Petra Němcová, Jessica White, Scarlett Johansson, and Shannon Costello.

Penn has been hard at work promoting his role as a philosophizing New York City cab driver called Clark opposite Dakota Johnson’s Girlie in Christy Hall’s critically-acclaimed, two-person drama Daddio – which will be released in limited US theaters this Friday.

Earlier this year, the Use Me actor reunited with his Licorice Pizza director Paul Thomas Anderson to shoot an untitled Warner Bros. ‘event film’ alongside Leonardo DiCaprio, Regina Hall, Teyana Taylor, and Alana Haim.

The contemporary IMAX movie is said to be the 53-year-old filmmaker’s ‘most commercial’ film to date and it’s already scheduled to be released August 2025.

The Asphalt City producer-star famously split from his second wife - eight-time Emmy nominee Robin Wright (L, pictured in 2005) - four times during their 21-year relationship - in 1995, 2007, and twice in 2009 - before finally ending their 13-year marriage in 2010

The Asphalt City producer-star famously split from his second wife – eight-time Emmy nominee Robin Wright (L, pictured in 2005) – four times during their 21-year relationship – in 1995, 2007, and twice in 2009 – before finally ending their 13-year marriage in 2010

Sean and his 58-year-old Crossing Guard leading lady (M, pictured in December) are proud parents of 33-year-old daughter Dylan Frances Penn (R) and 30-year-old son Hopper Jack Penn (L), but this was a point of contention during the divorce

Sean and his 58-year-old Crossing Guard leading lady (M, pictured in December) are proud parents of 33-year-old daughter Dylan Frances Penn (R) and 30-year-old son Hopper Jack Penn (L), but this was a point of contention during the divorce

By contrast, Penn remains amicable with his first wife - seven-time Grammy-winning pop diva Madonna (L, pictured in 2016) - whom he divorced in 1989 after three years of marriage

By contrast, Penn remains amicable with his first wife – seven-time Grammy-winning pop diva Madonna (L, pictured in 2016) – whom he divorced in 1989 after three years of marriage

The CORE co-founder noted: 'It turns out it's a lot quicker to repair a friendship after divorce if there are not kids involved. It took Robin and I quite a while. There was a lot of drama. Much more important to repair it if there are kids involved, but no easy swing, right?'

The CORE co-founder noted: ‘It turns out it’s a lot quicker to repair a friendship after divorce if there are not kids involved. It took Robin and I quite a while. There was a lot of drama. Much more important to repair it if there are kids involved, but no easy swing, right?’

Sean has been hard at work promoting his role as a philosophizing New York City cab driver called Clark opposite Dakota Johnson's Girlie in Christy Hall's critically-acclaimed, two-person drama Daddio - which will be released in limited US theaters this Friday

Sean has been hard at work promoting his role as a philosophizing New York City cab driver called Clark opposite Dakota Johnson’s Girlie in Christy Hall’s critically-acclaimed, two-person drama Daddio – which will be released in limited US theaters this Friday

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