Rosie O’Donnell‘s love life has been just as eventful as her career. She’s walked down the aisle twice, both times with women who played significant roles in her life. Her first marriage was to Kelli Carpenter, a former Nickelodeon marketing executive. They tied the knot on February 26, 2004, in San Francisco, during the brief window when the city was granting marriage licenses to same-sex couples before state law intervened.
Their wedding wasn’t just a personal milestone—it was a political statement. Rosie made it clear that President George W. Bush’s push for a constitutional amendment banning same-sex marriage was what propelled her to take the plunge. “We were both inspired to come here after the sitting President made the vile and hateful comments he made … [O]ne thought ran through my mind on the plane out here – with Liberty and Social Justice for all.” Their ceremony, officiated by city treasurer Susan Leal, one of San Francisco’s highest-ranking lesbian officials, was accompanied by the San Francisco Gay Men’s Chorus serenading them.
Rosie O’Donnell’s Wives and Children: A Look at Love, Marriage, and Family
Rosie and Kelli didn’t just blend their lives together—they built a family. Rosie had already adopted Parker Jaren O’Donnell in 1995, and Kelli later adopted him as well. Their family grew with the addition of Chelsea Belle O’Donnell in 1997, followed by Blake Christopher O’Donnell in 1999. Then, in 2002, they welcomed Vivienne Rose O’Donnell via artificial insemination. Despite their picture-perfect family, their marriage ended in 2007. Though their marriage was legally voided due to California’s legal battles over same-sex unions, they continued to co-parent their children. Kelli later married singer Anna Steele in 2013, with their son Parker walking his mom down the aisle.
Rosie’s second marriage was to Michelle Rounds, a corporate headhunter. They met in 2011 at a Starbucks, and sparks flew immediately. By December 2011, Rosie announced their engagement to her studio audience on The Rosie Show. However, before they could officially say “I do,” Michelle was diagnosed with a rare Desmoid tumor, requiring immediate surgery. On June 9, 2012, in a quiet, private ceremony, they married in New York before Michelle underwent treatment. Together, they adopted a daughter, Dakota, in January 2013, solidifying their family unit.
Unfortunately, their relationship unraveled, and in February 2015, Rosie filed for divorce. By October of that year, their divorce was finalized, but the emotional toll was significant. Rosie retained full custody of Dakota, while Michelle struggled with personal demons. In a tragic turn of events, Michelle died by suicide on September 11, 2017. Rosie spoke candidly about the tragedy, saying, “You think love has the answer, but mental illness has no say.”
Post-divorce, Rosie had a whirlwind romance with Elizabeth Rooney, a police officer and former Army veteran. They got engaged in October 2018, but their long-distance relationship—Elizabeth lived in Boston while Rosie was based in New York—proved challenging. By November 2019, the engagement was off. After that, Rosie briefly dated massage therapist Aimee Hauer, going public with their relationship in June 2022. They even made a red carpet appearance together at a comedy benefit in July. But by October of the same year, they had broken up, with Rosie scrubbing any trace of their relationship from her social media.
Beyond her relationships, Rosie’s role as a mother has been one of the defining aspects of her life. She’s been open about the joys and struggles of parenting, particularly with her daughter Chelsea. Chelsea ran away from home in 2015, and when she was found a week later, tensions between mother and daughter were clear. Their relationship has been rocky ever since, with Chelsea later getting married and having kids of her own. Unfortunately, Chelsea has also faced legal troubles, including multiple arrests in Wisconsin in 2024 related to drug possession and child neglect.
As a mother of five and now a grandmother, Rosie has found fulfillment in her evolving family. Parker followed his passion for military history and successfully convinced Rosie to let him attend Valley Forge Military Academy. Chelsea’s tumultuous journey has been painful, but Rosie has remained hopeful. Meanwhile, Blake and Vivienne have largely stayed out of the spotlight, enjoying a more private life. And Dakota, now the center of Rosie’s world, continues to be raised by her doting mother.
