Rosie O'Donnell Shares Texts With Daughter Chelsea as They Reconnect During Prison Stay

Rosie O’Donnell is letting fans see a softer moment in her complicated relationship with daughter Chelsea.

On August 27, the comedian, 64, shared an Instagram post featuring a throwback photo of herself hugging Chelsea, 28, along with screenshots of a recent text exchange between them.

The messages showed the two catching up while Chelsea remains incarcerated.

“Thank you mom I got my music back today. How are you?” Chelsea wrote. “I’m trying to get ahold of the social worker to let her know the plans for when i get out, Hannah texted her for me.”

O’Donnell answered with the kind of everyday update that made the exchange feel notably normal.

“Ok great — got my nails done — no more gel for me my nails are ruined,” she replied. “Are u reading a good book ?”

Chelsea told her mother she was reading the Legacy Series and enjoying it.

“I havnt painted my nails in years but I remember that stuff breaking my nails,” she added.

The post comes after O’Donnell and Chelsea began publicly discussing a new chapter in their relationship. In July, O’Donnell told Page Six that a recent prison visit marked a rare extended conversation between them.

“It was the first conversation I’ve had with her in 10 years that lasted more than 25 minutes,” O’Donnell said.

She said the four-hour visit was also the first time she had seen Chelsea “in a consistent way,” and that Chelsea cried when the visit ended early because of a tornado warning.

Chelsea, whom O’Donnell adopted as a baby in 1997, has had a strained relationship with her mother for much of her adult life. O’Donnell, who has five children, has spoken publicly about Chelsea’s early struggles and told Page Six her daughter was “born addicted” to drugs.

“I thought, ‘Well, love can cure everything,’ but I don’t know that that’s true,” she said.

Noting that she had been sober for two years at the time of their visit, O’Donnell said Chelsea had a “healthy calm.”

“That’s the first time I’ve seen, kind of, an empathetic emotion from her,” O’Donnell shared.

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

Chelsea had her probation revoked and was sentenced to prison in October 2025. In February 2025, she pleaded guilty to resisting or obstructing an officer, felony bail jumping and possession of methamphetamine.

She was sentenced in March to six years of probation and warned that violations could lead to prison time. Her probation was later revoked.