The Untold Story Of Rosie O'Donnell's Messy Personal Life

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This article contains references to substance abuse, suicide, domestic violence, and mental health issues.

Rosie O’Donnell has hosted an eponymous daytime chat show that picked up multiple Emmy Awards, starred in ’90s classics “A League of Their Own” and “Sleepless in Seattle,” and enjoyed recurring roles in “The Fosters,” “Curb Your Enthusiasm,” and “Nip/Tuck.” She’s also achieved success in the worlds of stand-up comedy, publishing, and philanthropy. But take a quick glance at her Wikipedia page, and you’ll notice that her life outside of the workplace has been even more eventful.

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The native New Yorker has certainly given the press plenty of headlines since rising to fame on the talent show “Star Search” in the mid-1980s. There have been two failed marriages (and another near-miss), long-running feuds with political figures, and a very public coming out, not to mention a continuing tabloid drama involving one of her five adopted children. Here’s a look at 14 times that O’Donnell’s personal life got truly messy.

After much tabloid speculation, Rosie O’Donnell confirmed in 2002 that, like her fellow comedian-turned-daytime talk show host Ellen DeGeneres, she was indeed a gay woman. Instead of coming out in a carefully planned magazine interview, the star decided to blurt out the news live on stage at a comedy club.

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“I’m a dyke,” O’Donnell declared to a crowd of no more than 250 people at Caroline’s on Broadway (via the New York Post). “I don’t know why people make such a big deal about the gay thing … People are confused. They’re shocked, like this is a big revelation to somebody!” “The Flintstones” actor also took aim at those who’d denounced her as a traitor to the LGBTQ community for not being open earlier. “‘Oh, but you were lying,’ the gay Nazis say. ‘You said you liked Tom Cruise.’ I said I wanted him to mow my lawn and bring me a lemonade! I never said I wanted [to perform a sex act on him].”

Several decades later, O’Donnell told “Red Table Talk: The Estefans” that by making her announcement so soon after the September 11 attacks, the news barely made a blip on the radar. “I’m like, ‘I’m gay,'” she recalled (via ET). “Listen, 9/11 happened, I’m gay. I’m telling you all, I’m gay. In case the buildings blow up again, I’m so, so gay, you know?”

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Love, money, green cards. There are many reasons why couples walk down the aisle together. In 2004, Rosie O’Donnell added another to the list when she got hitched to ex-Nickelodeon marketing exec Kelli Carpenter: politics.

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Yes, the pair decided to say “I do” in San Francisco in a protest against the support shown by 41st POTUS George W. Bush for the Federal Marriage Amendment. “We were both inspired to come here after the sitting President made the vile and hateful comments he made,” the “Another Stakeout” actor said just two weeks after the authorization of same-sex marriage licenses by the city’s mayor Gavin Newsom.

Later, O’Donnell acknowledged that legal paperwork had also been a factor in her decision to tie the knot. “We applied for spousal privilege and were denied it by the state. As a result, everything that I said to Kelli, every letter that I wrote her, every e-mail, every correspondence and conversation was entered into the record … I am now and will forever be a total proponent of gay marriage.”

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Rosie O’Donnell has always been candid about her mental health struggles, admitting she suffers from seasonal affective disorder, PTSD, and depression. And in 2007, she revealed she’d adopted an unorthodox way of attempting to keep the black dog at bay: hanging upside down every day for 30 minutes.

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O’Donnell even gave a demonstration of the inversion therapy technique while opening up on “The View,” the daytime talk she later vowed never to return to. And she also explained her battle with depression started in the wake of a national tragedy. “I couldn’t stop crying,” she told the panel (via CBS News) about the Columbine High School massacre, which left 13 people dead. “I stayed in my room. The lights were off. I couldn’t get out of bed, and that’s when I started taking medication.”

While O’Donnell strongly vouches for both inversion therapy and medication, she believes the most effective way of overcoming depressive thoughts is to keep active. “Like in “The Wizard of Oz” the color goes out,” the funnywoman added. “That is what happens in depression. Everything gets gray.”

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Just three years after walking down the aisle together in a political statement, Kelli Carpenter and Rosie O’Donnell sadly went their separate ways. And just as their nuptials had been based on an unorthodox reason, so had their split. In a 2010 interview with Oprah.com, the “Exit to Eden” star revealed a certain racket sport was partly to blame.

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O’Donnell recalled how Carpenter was insistent on joining their local country club with their four children to play tennis, the type of establishment that the former talk show host had previously given a wide berth: “I tried. They made an exception for a gay family, and we joined. It was a big thing. ‘They let in a gay family, whoo!’ So I show up to play with her, and somebody comes out and says, ‘You can’t play unless you have tennis whites.'”

O’Donnell also spoke about how hard it had been to admit her and Carpenter’s relationship had come to an end. “[The divorce was] Humbling. And humiliating,” she said. “In the O’Donnell family, no one had ever been divorced.” Of course, the pair had only been legally wed for six months. Just like thousands of other same-sex couples, their marriage certificate was voided in August 2004 by the California Supreme Court.

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Rosie O’Donnell experienced a major health scare in 2012 when she discovered she’d suffered a heart attack. In a candid blog post, the “Harriet the Spy” star admitted that she was “lucky to be here” after becoming ill at her New York home. In fact, if she hadn’t Googled her symptoms, things could have been very different.

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O’Donnell explained that after days of feeling feverish, nauseous, and achy, she searched online for the signs of a heart attack. The following day, she headed to a cardiologist who found an artery that was blocked all but one percent. The funnywoman, who’d suffered an attack described as a “widow maker,” was subsequently fitted with a stent.

Although O’Donnell didn’t call for an ambulance at the time that she felt unwell, she implored readers to do so if they experienced similar symptoms: “50% of women having heart attacks never call 911. 200,000 women die of heart attacks every year in the U.S. … Listen to the voice inside, the one we all so easily ignore, call 911.”

In 2012, Rosie O’Donnell walked down the aisle for a second time, on this occasion to Michelle Rounds, an IT staffing recruiter, in New York. Sadly, it didn’t prove to be second time lucky. Just three years later, the couple headed for the divorce courts, and they also later became embroiled in a bitter custody battle over their adopted daughter, Dakota.

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“Right now she has 24/7 nannies over there at Rosie’s house,” Rounds, who later married and had another daughter with Krista Monteleone, claimed to ET. “I don’t want my child to have a nanny. I want her to be outside playing, I want to be with her. I want to go to all the parent conferences and that’s just not what it’s about over there.” In response, O’Donnell argued that such talk was “an absurd and desperate attempt to use a child for her own gain.”

The situation became even more tragic in 2017 when Rounds committed suicide at her home in Florida at the age of just 46: two years earlier, she’d been taken to hospital following an overdose. In a statement given to USA Today shortly after the news of her ex-wife’s death, O’Donnell wrote, “I am saddened to hear about this terrible tragedy. Mental illness is a very serious issue affecting many families. My thoughts and prayers go out to Michelle’s family, her wife Krista, and their child.”

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In August 2015, Rosie O’Donnell took to social media to declare that her teenage daughter Chelsea hadn’t been seen in seven days. According to the “Beautiful Girls” star, the 17-year-old had fled with her therapy dog from their home in Nyack, New York, without any information on where she was going.

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Thankfully, Chelsea was soon found. But the situation only became more complicated. The youngster was discovered at the home of Steven Sheerer, a 25-year-old with an alleged heroin problem who was then arrested on charges of endangering a child’s welfare and distributing obscenities to a minor. The defendant, however, argued that he’d forged a consensual relationship with Chelsea, who he apparently believed to be 19 at the time.

Cindi Berger, a spokesperson for Rosie, claimed that the ordeal had occurred due to a skipping of vital medication. “Chelsea, like millions of people, lives with mental illness,” she said (via People). “It has been a difficult road for Chelsea and her family and they just want her back safe. [Rosie and Chelsea] have a good relationship. Rosie loves Chelsea very much.” Soon after, though, the teen successfully appealed against a no-contact order between her and Sheerer. She also decided to leave the family home in the Big Apple and reunite with her biological mom in Wisconsin. Sadly, this wouldn’t be the end of all the drama.

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Rosie O’Donnell once again made headlines for her eventful love life in 2017 when she began dating Elizabeth Rooney, a boxer and Army veteran 23 years her junior. And by the end of the following year, the May-December couple had put an engagement ring on it.

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“I keep telling her I’m too old for her,” O’Donnell once admitted to People about their generational age gap. “But she doesn’t seem to care. She’s like, ‘I was in the Army! I put my life on the line every day you think I don’t know who I want to date?’ I’m like, ‘All right I guess that’s true.’ She has a lot of good points.”

But before O’Donnell could make Rooney wife number three, the pair split. In November 2019, Radar Online noted how all the posts regarding their engagement had been removed from the former chat show queen’s Instagram page, as had the diamond ring emoji in her bio. It didn’t take long, however, for the star to get back on the saddle.

After several failed long-term relationships, Rosie O’Donnell decided to take a different approach to the dating scene in 2022. Impressed with massage therapist Aimee Hauer’s TikToks, the “Wide Awake” star slid into her DMs in the hope of striking up a real-world connection. And although the object of her affections took her time responding — ten days, in fact — the tactic ultimately worked.

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“Every time I saw her, I would smile and [be] like, ‘This woman is, like, perfect,'” she gushed on Howard Stern’s SiriusXM show (via People) about what initially attracted her to Hauer. “Look at her, she’s so happy and enthusiastic and beautiful and bright and she has a light coming from her.”

Hauer was flattered by the attention and eventually sent a video, which led to a physical meeting, and then things between the pair got even more serious. “I’m in love,” O’Donnell continued. “She’s really kind and wonderful, and I like the pace we’re going at. It’s not like a U-Haul situation.” The interview appeared to jinx things, however, as just a month later, the couple went their separate ways.

Here’s a celebrity friendship that no one could have possibly imagined. In 2025, Rosie O’Donnell revealed to The New York Times that she’d developed a close platonic relationship with none other than convicted murderer Lyle Menendez.

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The star had previously spoken up in defense of Lyle and his brother Erik, both of whom were found guilty of the 1989 first-degree murder of their parents. Indeed, while appearing on “Larry King Live” in 1996, O’Donnell argued that the siblings had simply acted in self-defense. After further expressing her support on TikTok, Lyle’s wife, Rebecca Sneed, arranged a phone meeting between the pair, which lasted a remarkable four hours.

“Then he started calling me on a regular basis from the tablet phone thing they have,” O’Donnell explained about how they kept their connection going. “He would tell me about his life, what he’s been doing in prison, and, for the first time in my life, I felt safe enough to trust and be vulnerable and love a straight man.”

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“So yes this is true,” Rosie O’Donnell began an Instagram post (via Us Weekly) in November 2024 following the news that her adopted daughter, Chelsea O’Donnell, had been arrested for the third consecutive month. “We all hope she is able to get the help she needs to turn her life around.”

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Chelsea’s run of legal woes began when she was arrested on several charges by Marinette County police, including domestic abuse, methamphetamine possession, and child neglect after her 11-month-old was discovered in a filthy, drug-filled home. Two months later, she was hit with five further felony counts in the same area, including bail jumping. In between, she got into trouble with Oconto County officials for several offenses, including obstructing/resisting an officer.

The tragedy of Chelsea O’Donnell got even sadder when she was later sentenced to six years of probation, with conditions including no possession or consumption of alcohol and no contact with anyone associated with drugs.

No one could accuse Rosie O’Donnell of failing to put her money where her mouth is. While many celebrities vowed to flee America once Donald Trump became president (or become president again) only to go back on their word once their worst nightmare happened, “The Flintstones in Viva Rock Vegas” star really did emigrate following the Republican’s election victory over Kamala Harris.

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Along with her son Clay and their beloved pet dog Kuma, O’Donnell relocated to Ireland in 2025 for the sake of both her family’s and her own sanity. So, what exactly is the real reason that the pair can’t stand each other? Well, the former talk show host has been locked in a feud with Trump ever since she called him out on “The View” back in the mid-00s.

“I mentioned his bankruptcies, I mentioned all of the sexual assault charges, and I mentioned that he was not, in fact, the businessman that everyone thinks he is because of the show, ‘The Apprentice,’ where they sold a bunch of lies to America for over 10 years, and half of America believed it,” O’Donnell explained to People (via Metro). The star, who once apologized to Trump’s wife Melania for insulting their son Barron, admitted that even two decades on, she can’t get used to the fact that the POTUS is still using her as a punchline.

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Rosie O’Donnell faced even more drama involving Chelsea O’Donnell, the troubled daughter she’d adopted as an infant with first wife Kelli Carpenter, in 2025. Only this time around, she instigated it. Yes, shortly before relocating to Ireland with her son Clay and their pet dog, the “Now and Then” star reportedly changed her will. And no prizes for guessing which family member was notably omitted.

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In fact, the former chat show host cut Chelsea out of two separate trusts, including the life insurance policy worth a cool $27 million. Of course, the new non-beneficiary didn’t take this lying down. In retaliation, she filed a petition to change her surname from O’Donnell to Neuens, the maiden name of her birth mother Deanna Micole.

The back and forth continued with a poem that Rosie posted on her blog titled “My child Chelsea.” Lines included “She wishes to change her last name/to her birth moms maiden name/doesn’t make sense to me/I am not her” and “But rain or shine/same name or not/that’s my girl/fierce and determined.” Despite the obvious tension between the pair, Rosie claimed that she was still immensely proud of Chelsea.

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Although she’s denied ever being an alcoholic, Rosie O’Donnell has vowed to give up the demon drink on several occasions. In 2008, for example, she revealed on her blog that she’d gone teetotal, and when asked why by an inquisitive reader, reeled off a list of entirely valid reasons.

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“Cause I was drinking too much, ’cause I didn’t want to any more, ’cause it is hard to lose weight when drinking, ’cause I can never have only one,” O’Donnell wrote (via People). The “Car 54, Where Are You?” star admitted that she didn’t find abstinence particularly easy but that she ultimately felt better.

However, her no-alcohol rule wasn’t lifelong. In 2025, O’Donnell revealed that she’d been relying on her favorite tipple a little too heavily in the wake of longtime foe Donald Trump’s second rise to the White House. But on relocating to Ireland where, thanks to her grandparents’ heritage, she’s potentially able to secure citizenship, she decided to once again swear off anything stronger than a lemonade.

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If you or anyone you know needs help with mental health, substance abuse, domestic abuse, or suicide, contact the relevant resources below: