Joshua Goldman
Joshua Goldman
min read · August 31, 2025 · Entertainment

Robin Wright on Parenting with Sean Penn: A Regret That Lingers

Robin Wright has reflected on the difficulties of parenting with her now ex husband Sean Penn (pictured in 2005)

SEAN PENN'S TURBULENT PARENTING SCANDAL ROCKS HOLLYWOOD

In a jaw-dropping interview, actress Robin Wright has opened up about the tumultuous years she shared with her ex-husband Sean Penn, revealing the shocking difficulties they faced as parents to their two children. The explosive revelations have left fans and insiders alike stunned, shedding light on the behind-the-scenes drama that plagued the power couple's relationship.

Robin, 59, and Sean, 65, had a whirlwind romance that began in 1989 after he split from his then-wife Madonna. Their on-again, off-again relationship culminated in a marriage in 1996, which lasted until their divorce in 2010. During their time together, they welcomed two beautiful children, Dylan Frances Penn and Hopper Jack Penn.

The actress, 59, and Sean, who divorced in 2010, share kids Dylan Frances Penn, 34, and Hopper Jack Penn, 32 (L-R: Dylan, Robin, Hopper)

In an interview with The Sunday Times, Robin candidly spoke about the struggles she faced as a parent to her kids, citing Sean's frequent absences due to work commitments as one of the main issues. "He was gone so much of the time," she revealed. "He'd come back and be the policeman, and then he'd leave me with the residue." This "extreme" parenting style left their children without a stable sense of discipline, forcing Robin to pick up the pieces when Sean was away.

But it seems that Sean's tough love approach had a lasting impact on their kids. Hopper, 32, has been open about his struggles with addiction in the past, revealing that he turned to crystal meth at one point and even spent time in rehab after a particularly rough stint. In an interview with ES Magazine, he shockingly revealed that it was Sean who coaxed him into seeking help. "I woke up in hospital and my dad said, 'Rehab? Or bus bench?' I was like, 'I'll take the bed.'" It's clear that Sean's tough love approach had its pros and cons.

Meanwhile, Dylan, 34, has followed in her parents' footsteps, pursuing a career in acting and modeling. But despite their efforts to keep the family drama under wraps, it seems that Robin regrets not being tougher on their children when they were younger. "I have a huge regret as a mother," she confessed. "I wasn't hard enough on them." These candid admissions have sparked a heated debate about the best parenting style, leaving fans wondering if Sean's strict approach was actually beneficial for their kids.

She said: 'He was gone so much of the time. He'd come back and be the policeman and then he'd leave me with the residue' (seen in 2009)

The Penns' relationship has been nothing short of tumultuous over the years. The couple met on the set of State of Grace in 1990 and had an on-off romance before marrying in 1996. When their relationship became too much to handle, they moved to a small town near San Francisco, where Robin stepped back from acting to focus on motherhood.

As it turns out, even when they were apart, Sean and Robin couldn't seem to stay away from each other. They wed in 1996, only to plan their divorce just four months later. However, they called off the divorce in December 2007, sparking rumors of a reconciliation. The couple eventually separated again in April 2009 but managed to put their differences aside long enough to finalize their divorce in July 2010.

Since his divorce from Robin, Sean has moved on with Australian actress Leila George, whom he married in 2020 and divorced just two years later. Despite his many high-profile relationships, it seems that Sean's most notable romance was with the woman who helped raise his children – Robin Wright.

Dylan and Sean seen in 2021. Dylan has worked as a model and an actress following in her parents' footsteps

Sean Penn's Hollywood career is no stranger to controversy either. The Santa Monica native made his film debut in the 1981 film Taps, which also starred George C. Scott and Tom Cruise. He has won Oscars for his roles in Mystic River (2003) and Milk (2008), cementing his status as a Hollywood A-lister.

As fans continue to dissect Robin's candid admissions about their parenting struggles, it's clear that the Penns' relationship was far from perfect. But one thing is certain – Sean Penn's tough love approach had its pros and cons, leaving an indelible mark on the lives of his children.