A Look Inside Rosie O'Donnell's Romantic History

Comedian Rosie O'Donnell has been married twice: She is a doting mother of four!  

A multiple Emmy-winning comedian and talk show host, Rosie O'Donnell, has been a fixated figure in Hollywood for many decades. She is also a producer, actress, author, and an outspoken advocate for LGBT rights. O'Donnel became known as the "Queen of Nice" as she catapulted to fame, hosting her syndicated daytime talk show, The Rosie O'Donnell Show.  

While Rosie's philanthropic efforts garnered her the sweet nickname, the comedian sparked as much controversy for her blunt, and brutally honest confrontation; once with Donald Trump. The Emmy-winning comedian is a lesbian and has been one of the most forthcoming Hollywood gay A-listers. 

Inside Rosie O'Donnell's Romantic History!  

Rosie's personal life has been one long affair in the spotlight. The comedian has had some high-profile romances over the years, and she has married two out of the trove. The Emmy winner became a mother way before she became a wife.   

In 1995, she adopted her first kid, Parker, later also adopted by Rosie's first wife, Kelli Carpenter. Rosie announced her sexual orientation shortly after playing a lesbian character in Will & Grace. Not to mention that she was one of the few to speak candidly on the frowned-upon subject, but also one of the minority to launch protests for gay parents' adoptive rights.  

She and her partner, Carpenter, a former marketing executive tied the knot on February 26, 2004, and went on to welcome three more kids, daughters Chelsea, Vivienne, and son Blake. The twosome's nuptial sailed smoothly for a few years, and they announced their split in 2007.   

Not much has been covered about the estranged couple since except that Carpenter remarried, and pursued a career as a producer. O'Donnell, on the other hand, suffered a similar fate in her next marriage. The Rosie O'Donnell Show host married her second wife, Michelle Rounds, in 2012.   

Rosie started dating Rounds, an executive search consultant, in mid-2011 and announced their engagement later that year. Following their intimate 2012 wedding, the couple adopted their daughter, Dakota, and unveiled their legal split, citing "irreconcilable differences," in 2015.    

The couple had navigated a tough time with their health scare in the years following their wedding. Rosie's then-wife, Dakota, received her desmoid tumor diagnosis and was in recovery when the comedian herself suffered a heart attack around the same time.   

O'Donnell's second ex-wife died of an apparent suicide in 2017. Rounds was 46 at the time of her death. The Emmy winner went public with police officer Elizabeth Rooney in late 2017. And even announced their engagement a year later, but sadly, the couple's relationship never made it to the alter.  

Who is Rosie O'Donnell Dating?  

Sadly, the Star Search actress hasn't experienced the same luck in her love life. After her romance with Rooney came to an end in 2019, O'Donnell fell in love and got candid with Tik Tok influencer, Aimee Hauer, in 2022. 

The comedian first started off by fueling a swirling romance rumor after she posted a snap of her holding hands with a mystery woman, later identified as Hauer. The love birds shortly went official, posting a selfie on Instagram, and made their red carpet debut the same year.  

The adorable couple was so in love that Hauer even got Rosie's initial "R" tatted. During Rosie's appearance on The Howard Stern Show, in September, the Emmy winner even gushed about her new beau. "I watched her TikToks and every time I saw her, I would smile," the stand-up comedian said.  

O'Donnell further adds, "She's so happy and enthusiastic and beautiful and bright and she has a light coming from her." But the romance didn't last long as the duo revealed their split later that month. Rosie later expressed disappointment over her one more failed relationship.  

"I wish I had been able to have a relationship that lasted forever, but I think I didn't have the capability for a lot of reasons," the comedian said. Rosie even explained how she always admired others' enduring relationships and envied them for it. The ardent LGBTQ advocate talked about never walking down the aisle again. 

Who are Rosie O'Donnell's Five Kids?  

"I kind of like being a single parent," the 61-year-old said in her latest interview. Rosie has been open and honest about her excruciating, yet rewarding journey as a parent. The comedian has welcomed five kids across her two marriages and the parenting hasn't been easy.   

She and her first wife, Carpenter, welcomed Parker, 28, Chelsea, 25, Blake, 23, and Vivienne,20, during their three-year-long marriage. Parker has made some public appearances with his famous mom in the past but mostly stays out of the limelight. Rosie once revealed that her son is in the Marines. 

Rosie and Carpenter's daughter, Chelsea, has been in the spotlight numerous times. Rosie's troubled relationship with Chelsea was usually the subject of their public family moments. At one point, Chelsea even disappeared and was later found with her birth mother.  

The mother-daughter duo reconnected after years of strained relationship during Chelsea's pregnancy. Chelsea's daughter and Rosie's first grandchild was born in December 2018. She has since welcomed two more girls. Rosie's third kid, Blake, began attending Marist College in New York, in 2018.   

The Emmy-winning comedian adopted her youngest kid, Dakota, in 2013! 

O'Donnell often gushes about her son, who, on the other hand, keeps it on the low. The comedian announced her son's engagement to his longtime girlfriend, Teresa, in a post. The View alum's second youngest, Vivienne, is enrolled at the University of Delaware.  

The comedian shares an endearing relationship with her Vivienne, with the duo often appearing on each other's Tik Tok. O'Donnell's youngest, Dakota, 9, is undoubtedly the apple of Rosie's eye, and Dakota's frequent appearance on the actress's social media pages is enough proof.  

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