Rosie O'Donnell's 5 Kids: Everything to Know

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Rosie O'Donnell is both a mother and grandmother.

The actress and comedian has welcomed five children since 1995: Parker, 27, Chelsea, 25, Blake, 23, Vivienne, 20, and Dakota, 9.

But between teenage drama, public spats and custody battles, it hasn't always been an easy ride for the star. "My teenagers are a nightmare, they're horrible," she joked in 2016. "I had four teenagers when I decided to adopt a newborn baby. You might ask why. Because I had four teenagers and I needed to remind myself that I actually do love children."

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In 2022, O'Donnell opened up to PEOPLE in a personal essay about her youngest daughter's autism diagnosis, writing, "Dakota's autism forces me to see the world from a completely different place. She's a gift from another dimension. ... To be able to see the world as she does — for me, it's been a wonderfully magical experience. I'm so glad we have each other."

On March 4, 2023, O'Donnell celebrated National Son's Day by paying tribute to Parker and Blake on Instagram.

"national sons day?! i love my boys blake n parker," she wrote.

Here's everything to know about the O'Donnell family.

Parker Jaren O'Donnell, 27

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O'Donnell adopted her first child, Parker O'Donnell, in 1995. He was born on May 25, 1995. The comedian was initially a single mother to Parker, but her former wife Kelli Carpenter later became his legal parent, too.

Parker enrolled in the Valley Forge Military Academy and is currently in the Marines. "How do you annoy your left-wing, liberal, pacifist mother? You become a big military man," she joked on The View in 2014.

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He is also a devoted partner to his longtime love, Hannah. In October 2021, O'Donnell shared a sweet picture of the couple with the caption, "happy 7th anniversary to parker n hannah #kidsgrownup."

Chelsea Belle O'Donnell, 25

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Chelsea Belle O'Donnell was born on Sept. 20, 1997, and was adopted by O'Donnell and Carpenter as a baby. Although they appear to have reconnected, The View alum and her eldest daughter haven't always had the easiest relationship, as they were estranged on and off throughout Chelsea's teenage and early adulthood years.

In August 2015, O'Donnell announced Chelsea had gone missing from their New York home. She was found a week later and subsequently moved to Wisconsin to live with her birth mother, Deanna Micoley. "Chelsea made a decision when she turned 18 that she wanted to go to her birth mother. This was her choice," O'Donnell's publicist Cindi Berger told PEOPLE at the time.

The comedian maintained her wish for her family was one for "love and peace."

In 2017, Chelsea sat down for an on-air interview with Inside Edition alongside her then-husband Nick Alliegro. "Growing up, I never really got along with her and then once she kicked me out, I was just kind of done," she said. "I miss the rest of my family a lot but I think there is some much-needed space between me and Rosie. It's been nice having that," she added.

The following year, O'Donnell and Chelsea reconnected over Chelsea's pregnancy. After Chelsea's boyfriend Jacob Bourassa shared a picture of the sonogram on Facebook, a rep for O'Donnell told PEOPLE they had begun to reestablish contact.

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Chelsea gave birth to a baby girl, Skylar Rose, in December 2018. The comedian was overjoyed to become a grandparent for the first time, tweeting, "My daughter chels – jake – and skylar rose my first grandchild !!! #love #life #NANA," along with a picture of Chelsea and Skylar in the hospital.

"It was something really beautiful," O'Donnell said of becoming a grandmother. "It's very trite, but it's what everyone says — when you're a grandparent, it's like [having] a baby times a million. And that's what it felt like."

In 2018, the star opened up about her relationship with her daughter on The Talk, saying, "I think with my relationship with my daughter, Chelsea, (the relationship being tested did make it stronger) because we went through some really public troubled times. She's doing better now and we're both communicating with each other. When somebody does something unforgivable to you and you can forgive them and they can forgive you, there's a kind of grace that descends upon the both of you, within that."

Chelsea is now mom to three girls, after welcoming baby Riley in January 2021 and baby Avery Lynn in February 2022.

Blake Christopher O'Donnell, 23

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The youngest boy of the O'Donnell bunch, Blake keeps his life very private. Born on Dec. 5, 1999, he was the third child that O'Donnell and Carpenter adopted together during their relationship.

"Dropped off my boy at college. Hard to believe," she tweeted in 2018, when he began attending Marist College in New York. A year later, O'Donnell told the sweet story of when Blake first watched her 1992 film A League of Their Own: "My son was at a party, and he comes home and he goes, 'Mom, I saw you on TV. You were in a baseball game, and you were a teenager,' " she shared with Page Six. "I'm like, 'Honey, that was my first movie. I was not a teenager. I was 29 years old.' "

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Blake does make rare appearances on his mother's social media, like this sweet Instagram carousel from August 2021 with his little sister Dakota and girlfriend Teresa, which O'Donnell captioned: "we r family ❤️👋🏽😜 #la."

On Dec. 19, 2022, Rosie announced her son's engagement in an Instagram post. Blake proposed to his girlfriend, Teresa Garofalow Westervelt, during a Broadway performance of Phantom of the Opera. Rosie included a photo of Blake down on one knee in a theater aisle plus a snap of Hillary Clinton smiling with the newly engaged couple.

"last night - my son blake asked his gf teresa to marry him - and she said yes !!! the crowd clapped - and hillary clinton was there too- i cried all through phantom of the opera - wishing my mom was here to see it all #love #family ❤️❤️❤️," she captioned the post.

Vivienne Rose O'Donnell, 20

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Vivienne is the fourth child O'Donnell shares with ex-wife Carpenter. She was born on Nov. 29, 2002, and is now enrolled at the University of Delaware.

When Vivienne graduated from high school in 2021, her mother just couldn't contain her pride. "Vivi and jackie - as vivi graduates from hs - hard to believe- im so proud of u honey - u r a wonderful young woman #vivi #graduation #love," O'Donnell wrote on Instagram.

Vivienne and her mother share a passion for social media, as O'Donnell revealed they spent time learning TikTok dances during quarantine. "I'm in the middle of a pandemic with a 17-year-old, trying to make her happy," she told Seth Meyers.

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In 2022, Vivienne made headlines after she said her upbringing was not "normal" on TikTok. She told her followers, "I love all these comments about how Rosie kept my life 'normal.' No offense, Mom, that never happened. She just didn't really inform us, for really anything."

O'Donnell readily admitted Vivienne's childhood "wasn't a normal (one) like all of her friends." In a candid TikTok, the Roseanne actress said, "It's okay, you're allowed to express your feelings in our family, even if you do it online in a funny manner."

In another TikTok, Vivienne shared the hilarious story of how she realized the family friend she knew as "Mo" was none other than Madonna. "At my birthday parties, this beautiful woman would always come, and I was like, 'Yeah, there's Mo,' " she shared. "I never had any idea who the f--- she was. … Then I find out it was Madonna all these years."

Dakota O'Donnell, 9

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Less than a year after O'Donnell married her second wife, Michelle Rounds, the couple adopted Dakota, who was born on Jan. 5, 2013. "We r thrilled to announce the arrival of r daughter Dakota - #withloveandthanks - AMEN," O'Donnell announced on Twitter.

In 2015, O'Donnell filed for divorce from Rounds on the grounds of "an irretrievably broken relationship," according to documents obtained by PEOPLE at the time. Rounds sought sole custody of Dakota, but then tragically died of suicide in 2017. "I am saddened to hear about this terrible tragedy," O'Donnell told PEOPLE in a statement. "Mental illness is a very serious issue affecting many families. My thoughts and prayers go out to Michelle's family, her wife and their child."

The youngest of O'Donnell's children, Dakota is a frequent mainstay on Rosie's social media. In a series of sweet TikToks, O'Donnell shared the reason why picking Dakota up from school is so important to her.

"You know, I have a lot of anxiety about that," she said of pickup time. "I think because having my mom die when I was little and then my dad, after work, it was tough to get picked up on time. So I have a thing about getting picked up on time."

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In September 2022, O'Donnell penned an emotional essay for PEOPLE and opened up about Dakota's autism diagnosis for the first time.

"I didn't want Dakota to feel shame about her diagnosis," O'Donnell shared. "I have told her from the start that autism is her superpower."

She added, "I am learning to have compassion much deeper than I ever did. To really listen and communicate in a way I never had to with my other kids. The sense of vulnerability that comes with having a kid with autism has been a gift to me. She teaches me."

The comedian also recalled the moment that Dakota asked to meet her birth mother. "We're in contact, so Dakota gets on FaceTime and says, 'Are you the lady whose tummy I was in? I just wanted you to know I'm the kid that was in there, and when I got born, my mommy held me and I squeezed her pinkie, and I am with her. So I just want to let you know that's what happened to me. Bye,'" O'Donnell recalled.

"I was in tears as was her birth mom," she wrote. "That's a pretty intense, complex, emotional thing for a little girl to put together." Speaking about all her children, O'Donnell added, "I think about the birth mothers every day."