Cheryl Hines & RFK Jr.'s Marriage Has Some Glaring Red Flags We Just Can't Ignore

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Cheryl Hines and Robert F. "RFK Jr." Kennedy Jr.'s controversial marriage is full of undeniable red flags — including relentless divorce rumors. In 2024, a decade after they tied the knot, a source told People amid rumors of infidelity from the political figure (more to come on that), "[Hines has] been talking about filing for divorce, but he's begging her not to file." They added, "But how many times can you forgive a partner that's dishonest and goes behind your back? It's just ridiculous behavior from a grown, married man." Two years before that, Radar Online claimed Hines was feeling the pressure to divorce her husband over his controversial remarks (there's more to come on that, too).

But while the couple are yet to head to splitsville, we've noticed countless reasons why their marriage could end up there. From various infidelity claims to the duo being very different people, there are so many aspects to Hines and Kennedy Jr.'s marriage that are troubling.

You don't have to do a major Google deep dive to find out about the cheating allegations that have swirled around Robert F. Kennedy Jr., as he's been accused of stepping out on Cheryl Hines multiple times. In 2017, Radar Online suggested RFK Jr. may have cheated with Chelsea Chapman Kirwan. Then, in 2024, journalist Olivia Nuzzi shared a statement to CNN that read, "Earlier this year, the nature of some communication between myself and a former reporting subject turned personal ... The relationship was never physical but should have been disclosed to prevent the appearance of a conflict." Though she didn't explicitly name RFK Jr., sources claimed to New York Post the two had been sending raunchy messages. In response, Kennedy Jr.'s spokesperson said, "Mr. Kennedy only met Olivia Nuzzi once in his life for an interview she requested, which yielded a hit piece." Following that bombshell, Mediaite reported three other women claimed to have had romantic relationships with the political figure in the 12 months prior.

Equally, Kennedy Jr. reportedly joined the roster of celebs who admitted cheating on their partners while married to his second wife Mary Richardson Kennedy. In a diary entry, made public by New York Post, RFK Jr. had supposedly written down the names of multiple women he's believed to have been romantically involved with during their marriage.

Robert Kennedy Jr. moved on from his marriage to Mary Richardson Kennedy with Cheryl Hines but faced allegations he didn't exactly sever ties with his former wife once they divorced. "Mary was brainwashed, believing everything that Bobby said. And he was leading her on," a source told Daily Beast. "He might have been with Cheryl [Hines, his girlfriend during Richardson's final years], but he was still giving Mary enough encouragement to stay hopeful ... Bobby did everything he could to demean and hurt Mary," they added. That proves why breaking free from an ex may be better than holding out hope for a friendship.

Though being friendly with a former partner isn't always a problem, if Kennedy Jr. failed to set boundaries with his ex and let her think there was a chance of a reconciliation, that's a problem and suggests he didn't truly respect Hines or Richardson Kennedy. "If your partner has a cordial, friendly relationship with [their ex,] that shows the person you're dating is mature, especially if there are children involved. However, if your partner is really good friends with their ex, I would definitely look into the circumstances," David Bennett, certified counselor and relationship expert, told Bustle.

When Cheryl Hines and Robert Kennedy Jr. got engaged, she gushed to Us Weekly, "We share the same values." She later told The Hollywood Reporter, "I liked that when we got together, we were from two different worlds." But things seemingly changed, as Hines admitted she didn't totally know the political figure's mind for a while. After being asked, "At what point in your relationship did you start thinking, 'Bobby has some very radical or novel ideas?'" she responded, "I guess a few years into it." A source also told Radar Online in 2017 that Hines didn't realize what she'd signed up for entering the Kennedy family. "Cheryl had no idea what she was getting into when she married Bobby," they said.

Their differences became clear in 2022 when the actor publicly distanced herself from her husband's views. "My husband's opinions are not a reflection of my own. While we love each other, we differ on many current issues," the "Funny You Should Ask" star wrote on X, formerly Twitter, after he made controversial remarks about the Holocaust. The two also clashed after RFK Jr. shared his support for president Donald Trump. "This is the opposite of what she would want to do," Kennedy Jr. told TMZ. "She went along with it because she loves me and she wanted to be supportive of me, but it was not something that she ever encouraged."

If they find they're constantly butting heads over opposing views, it could be a red flag. "If your non-negotiables oppose each other and you and your partner exhausted all options in terms of trying to find [a] middle ground, [it might be time to consider breaking up]," Anita A. Chlipala, LMFT, a relationship therapist, told Very Well Mind.

When Cheryl Hines and Robert F. Kennedy Jr. first met, they were still married to other people. They were introduced by Hines' "Curb Your Enthusiasm" co-star Larry David, but it took three separate meetings before things turned romantic. However, RFK Jr. appeared to suggest in a The New York Times interview that the actor was still with her first husband when they got together. "I was separated at the time, and Cheryl was still married," he said. He later told The Hollywood Reporter, "As soon as I saw her, I was, like, smitten." Seeing as both were legally married at the time, embarking on a romance suggests neither had much respect for their respective spouses — especially if Hines wasn't officially separated.

However, the "Suburgatory" actor has a slightly different take on how their relationship evolved. She claimed they were both very much broken up with their spouses and were going through divorces when they got together. "I saw in the paper that Bobby was going through a divorce, too," she said. "And I remember thinking, 'Oh, that's interesting. We're going through the same thing.'" 

Everyone deserves a second (or third) shot at love, but, as we learned with Jessica Simpson and Eric Johnson, it can be a red flag if someone has been married before. Cheryl Hines was married once before finding love with Robert F. Kennedy Jr. (to Paul Young from 2002 until 2010) and Kennedy Jr. tied the knot twice, first with Emily Ruth Black between 1982 and 1994 and then to Mary Richardson Kennedy from 1994 until 2012.

The issue with repeated walks down the aisle is it suggests they may not take the sanctity of marriage seriously or they aren't learning from their mistakes. It could even hint at an even deeper psychological issue. "Occasionally, when a person habitually enters into marriage multiple times, it could be that they may have an underlying mental health disorder, personality disorder, or attachment wounds that have left them feeling vulnerable — so they tend to fall into unhealthy relationship patterns," psychologist Andrea Sartor told Metro.

In RFK Jr.'s case, it's how quickly he moved on from his first wife to his second that has us concerned. In "RFK Jr.: Robert F. Kennedy, Jr. and the Dark Side of the Dream," it's claimed he proposed to Richardson Kennedy while still legally married to Black. Once he was officially divorced, Richardson Kennedy was six weeks pregnant and they married three weeks later. In a statement, RFK Jr. denied some claims made in the book, but didn't clarify which ones. "This book, written by a National Enquirer reporter, is a fictional inventory of unsubstantiated rumors and outright invention," he wrote on his website (via Page Six). If the timeline checks out though, it doesn't exactly give us hope for his romance with Hines.