Rosie O'Donnell on reuniting with her daughter in prison and their first long conversation in years

Rosie O'Donnell has opened up about visiting her daughter Chelsea in prison, revealing it marked their first meaningful conversation in a decade.

The comedian told Page Six that the reunion "was the first conversation I've had with her in 10 years that lasted more than 25 minutes."

Chelsea, 28, is currently serving time after her probation was revoked in October, having previously faced felony charges including bail jumping, resisting or obstructing an officer, and possession of methamphetamine.

O'Donnell explained that the prison visit was the first time she had properly reconnected with her daughter saying: "The first time that I saw her in a consistent way was the four hours in the prison."

She added that Chelsea cried when the visit was cut short by a tornado warning.

Rosie O'Donnell has opened up about visiting her daughter Chelsea in prison, revealing it marked their first meaningful conversation in a decade (Photo by Bruce Glikas/Bruce Glikas/FilmMagic)

Why is Chelsea O'Donnell in prison?

Chelsea was sentenced to six years' probation in February 2025 after appearing in court and was warned at the time that prison was a possibility if she breached her conditions.

That October, her probation was revoked and she was sentenced to jail.

O'Donnell said Chelsea has now been sober for "almost two years now and that's a very big part," reflecting on adopting her daughter as a baby and admitting, "she was born addicted, and when I was adopting, I thought, 'Well, love can cure everything,' but I don't know that that's true."

O'Donnell said her daughter Chelsea has now been sober for "almost two years now" (Photo by Raymond Hall/GC Images)

What did Rosie O'Donnell say about visiting her daughter in prison?

O'Donnell wrote a poem about the visit, describing the strict conditions she was given on arrival: 'The guard explained the rules,' she wrote, listing 'a hug hello and goodbye only,' with 'no money exchanged,' 'hands above the table,' and 'no loud voices.'

She went on to describe her heart skipping a beat upon seeing her daughter, who she said looked good and exuded a 'healthy calm'.

Reflecting on the visit, O'Donnell said it was the first time she had witnessed 'an empathetic emotion' from Chelsea, adding, So, you know, she's growing up', and saying she hopes 'her future is brighter than this past decade has been.'

O'Donnell adopted Chelsea as a baby and has four other children: son Parker, 31, son Blake, 26, daughter Vivi, 23, and her youngest, Clay, 13. (Photo by Bruce Glikas/WireImage)

How many children does Rosie O'Donnell have?

O'Donnell, who has four other children alongside Chelsea, revealed she is now working on a one-woman show centred on their relationship, and said she has asked for Chelsea's input on the project, explaining she wants her daughter's 'voice heard.'

O'Donnell adopted Chelsea as a baby and has four other children: son Parker, 31, son Blake, 26, daughter Vivi, 23, and her youngest, Clay, 13.

She revealed she is now working on a one-woman show centred on her relationship with Chelsea, and said she has asked her daughter for input on the project, explaining she wants Chelsea's 'voice heard' in how their story is told, adding that she believes her daughter is finally "ready to do that now."

The update comes as O'Donnell prepares to open her current show, Common Knowledge, on Broadway later this month, which touches on her childhood, motherhood and her move to Ireland.

The comedian has previously spoken about her decision to relocate, saying she 'wasn't nervous' about the move because of what she had read about Project 2025 and its potential impact.