Rosie O’Donnell’s Son Got Down on One Knee with ‘Grandmother’s Ring’ to Propose to His Girlfriend

• Rosie O’Donnell’s son got engaged!

• “I’m a nana. I love it,” Rosie said while talking about her grandchildren.

On December 19, 2022, Rosie O’Donnell, then 60, shared an Instagram post with two pictures of her son, Blake Christopher O’Donnell. In the first image, the star’s youngest son was on one knee holding up a ring to his girlfriend.

Rosie explained that on December 18, 2022, Blake had asked Teresa Garofalow Westervelt to marry him, and she’d agreed! The then-23-year-old man proposed in New York City while attending Broadway’s “Phantom of the Opera” musical.

The comedian revealed how the crowd had clapped and that even former United States Secretary of State Hillary Clinton was there to witness the special moment. The second image in Rosie’s post showed her son and Garofalow Westervelt posing with Clinton.

The actress said she’d cried throughout the musical while wishing her mother had also been there to see it. Blake was dressed in a long brown coat, a navy blue button-down shirt, khaki pants, and matching shoes.

Garofalow Westervelt wore a black top and burgundy pants and had on a Burberry scarf. Rosie’s ex-wife, Kelli Carpenter’s current wife, Anne Steele, also shared on social media how Blake had proposed with Carpenter’s “grandmother’s ring.”

Besides being a mother to Blake, Rosie had other older children that she shared with her ex-wives. In 2022, all her children were still under 30, and her youngest was a girl.

Rosie Is a Mother of Five

Since 1995, Rosie welcomed five children, including Parker Jaren, 27, in 2022, Chelsea Belle, 25, Vivienne Rose, 20, and Dakota, 9. Parker, born on May 25, 1995, was adopted the same year he was born.

The actress welcomed him as a single mother before Carpenter became his shared legal parent. He was in the Valley Forge Military Academy, joined the Marines, and had a relationship with Hannah.

In October 2021, the couple celebrated seven years together. On September 20, 1997, Chelsea was born, and Rosie and Carpenter adopted her when she was a baby, with her and the former not having the most effortless bond in the past.

Throughout Chelsea’s teenage years and early adulthood, she and “The View” alum had an estranged on-and-off relationship. In 2015, the star’s child went missing from their home and was found a week later before relocating to Wisconsin at 18 to be with her birth mother.

In 2018, Chelsea and Rosie reconnected when the former became pregnant with Jacob Bourassa’s baby. A representative said mother and daughter were rebuilding their relationship, and Skylar Rose was born that year.

The comedian was thrilled to be a first-time mother and said her relationship with Chelsea had strengthened. Rosie shared how her daughter was better, and both were communicating, and Chelsea welcomed Riley in January 2021 and Avery Lynn in February 2022.

Blake, born on December 5, 1999, was adopted while Carpenter and Rosie were still an item. He went to New York Marist College in 2018, and Vivienne was born on November 29, 2002, and was enrolled at the University of Delaware as of 2022.

On January 5, 2013, Dakota was born, and less than a year after marrying her second wife, Michelle Rounds, Rosie adopted the little girl who was autistic. Two years later, the actress filed for divorce, and Rounds wanted sole custody but died in 2017.

In the clip also shared on Rosie’s [O’Donnell] Instagram account, she showed exasperation over the little girls all being under three!

Having many children allowed Rosie to become a grandparent to many grandchildren. The star proudly shared the news of her grandchildren’s births and celebrated the exciting role.

“I’m a Nana. I Love It”

In December 2022, Rosie was a grandmother to three grandchildren. Her oldest granddaughters, Riley, then two, and Skylar, then four, are often featured on her social media accounts, like in one image where the two sat side-by-side in a booth.

The two girls wore matching long-sleeved white shirts with red overalls. When Avery was born, the comedian congratulated her daughter via a TikTok video, adding:

“I’m a nana. I love it.”

In the clip also shared on Rosie’s Instagram account, she showed exasperation over the little girls all being under three! The star also revealed that the family of five was doing well and asked to be called “Nana 3.”

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