Rosie O’Donnell says prison visit with daughter was their first real conversation in 10 years

Key Points

• Rosie O’Donnell reveals that prior to visiting daughter Chelsea in prison, they had barely spoken in the previous 10 years.

• “The first time that I saw her in a consistent way was the four hours in the prison,” the comedian told Page Six.

Rosie O’Donnell is revealing the significance of her emotional prison visit with her estranged daughter, Chelsea.

The comedian, who last month opened up about visiting her 28-year-old daughter in prison, has revealed that the chat marked a turning point in their relationship. In a Sunday interview with Page Six, O’Donnell shared that the behind bars visit with her daughter “was the first conversation I’ve had with her in 10 years that lasted more than 25 minutes.”

The mother of five continued, “The first time that I saw her in a consistent way was the four hours in the prison.”

Chelsea, who has struggled with addiction, was sentenced to prison time after her probation was revoked on Oct. 22, 2025. She was previously arrested three times between September and November 2024 on multiple drug charges. She eventually pleaded guilty to one felony count of bail jumping, one felony count of possessing methamphetamine, and one misdemeanor count of resisting or obstructing an officer.

O’Donnell said that the emotional conversation — which was cut short due to a tornado warning — was “the first time I’ve seen, kind of, an empathetic emotion from her.” When they were forced to cut the visit short, O’Donnell said Chelsea cried.

She continued, “So, you know, she’s growing up, and I hope that her future is brighter than this past decade has been.”

O’Donnell and her ex-wife Kelli Carpenter adopted Chelsea when she was a baby, raising her until 2015, when the 17-year-old ran away from home, only to be found a week later with her then-boyfriend. That same year, she moved to Wisconsin to live with her birth mother. In the aftermath, O’Donnell was estranged from her daughter until they reconnected in 2018, amid Chelsea’s pregnancy with her first child.

O’Donnell previously recounted visiting her daughter in prison with a poem shared on social media. In it, she described her complicated feelings about the reunion, writing, “I have tried to prepare myself / I know it will be difficult / But I must / As she asked me to / A first for her at 28 years old.”

The A League of Their Own alum went on to recount arriving at the prison early, noting, “The guard explained the rules / A hug hello and goodbye only / No money exchanged / Hands above the table / No loud voices.”

She wrote that upon seeing Chelsea enter the visitation room, her heart “skip[ped] a beat.” O’Donnell described her daughter as looking healthy, calm and well-rested. She said that they shared a long embrace and then spent hours talking.

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O’Donnell went on to express “hope” for her daughter’s future, writing, “She’s not fighting it anymore / This relationship we have. / Her sobriety helps so much / Gives me hope / and hope dies slowly / For families of addicts.”

She shared that since the visit, her daughter “calls daily,” writing that they have grown closer in recent months.

Read the original article on Entertainment Weekly