A Look At Martha Stewart's Tragic Relationship History

As anyone who watched "Martha" on Netflix will know, Martha Stewart's relationship history isn't exactly the stuff of romance novels. In fact, there are a ton of sad details about Martha's love life, and she's even admitted to being devastated by the two big heartbreaks she's endured. That said, she does also have a degree of nonchalance about the nature of her relationships.

Around 40 minutes into the "Martha" documentary (which Martha told The New York Times she hates, BTW), the legendary homemaker delivered a truth bomb we doubt anyone saw coming. Asked if she'd ever been in a relationship where she actively spoke about how she felt with her partner, Martha answered with a resounding "no" — and she added that this is because it isn't exactly her idea of a good time. "I couldn't care less," she chuckled. "I don't know what the real reason is ... It doesn't interest me so much to know, you know, 'Oh, Charles, how do you feel this second?' I don't care, actually," she admitted. Honesty is the best policy, we guess! Martha mused that it was likely because of her disinterest in talking about feelings that she hasn't been in many serious relationships. 

That said, it wouldn't be entirely accurate to say Martha hasn't been in any serious relationships. Quite the contrary, she was married to Andrew Stewart for almost three decades. After that, she was in another high-profile relationship with Charles Simonyi. However, both ended badly for the businesswoman. 

Martha Stewart revealed in "Martha" that she fell head over heels for her husband, Andrew Stewart, while she was in college. One of the major reasons she loved him so much, she explained, was because of his kindness — the polar opposite of her father, who was incredibly strict, and as she shared in the Netflix documentary, "Mean. Mean."

The twosome became inseparable, and Andrew ended up proposing. However, Martha's father wasn't exactly on board. "I went home and told my dad, and my dad slapped me ... slapped me hard, on my face, and said, 'No, you're not marrying him. He's a Jew!' I remember getting that slap," she recounted. Martha added that she wasn't particularly shocked by her father's refusal or reaction, explaining, "He was a bigot." Nevertheless, she was undeterred, and she and Stewart tied the knot anyway. 

That's not to say the relationship didn't have some red flags early on, though. Part of their five-month honeymoon fell over the Easter period, and Martha headed to the Cathedral of Santa Maria del Fiore for a service. She described the experience as an incredibly emotional one ... and evidently, a young man she met at the Duomo felt the same. "It was unlike anything I had ever experienced. An expansive dome, so beautiful, and paintings all around you, it was like nothing I had ever done before. And so, why not kiss a stranger?" she shared. And that, she did. However, she didn't see it as an act of infidelity. "It was just emotional, of the moment," she reasoned.  

Unfortunately, her kiss with a stranger at the Duomo wasn't the only unconventional thing that went down in Martha Stewart and her ex-husband's marriage. Speaking of Andrew's own indiscretions in "Martha," Martha shared that he had countless girlfriends after they moved to Westport, Connecticut. The businesswoman also hinted at wishing she'd ended the relationship as soon as she'd learned of the affairs. "Young women, listen to my advice: If you're married and you think you're happily married, and your husband starts to cheat on you, he's a piece of s***. And look at him as a piece of s*** and get out of it," she urged.

Here's the plot twist: Martha's kiss at the Duomo didn't mark the last time she explored outside her marriage, either. Au contraire, Martha admitted in "Martha" that she'd had a brief entanglement with another man while she was a stockbroker. However, she compared it to the Easter Eve kiss, claiming it didn't mean anything to her. "It was nothing ... I would never have broken up a marriage for it," she mused. Stewart didn't remember telling Andrew about it, but the "Martha" interviewer did say Andrew had told him he'd only begun having affairs after her admission. Martha wasn't convinced. 

"Martha" wasn't the first look into the Stewarts' infidelities. In fact, in the 1997 biography "Martha Stewart: Just Desserts," author Jerry Oppenheimer hinted at a different version of the homemaker's Duomo story. Though in "Martha" she said the man she'd kissed didn't know she was married, Oppenheimer claimed she and Andrew were staying at the same accommodation as him. Moreover, he wrote that after a few drinks, Martha and the unnamed man went out together without Andrew, then said they'd gone to Mass — but Andrew wasn't convinced, either. 

Even with all the drama, Martha Stewart never believed her marriage to Andrew Stewart would actually end. As such, when it did end, she was horrified. And, even though "Martha" began with her joking about not being interested in sharing feelings with her partners, she later said that actually talking about her attempts at keeping the marriage together was too difficult for her. Even so, she did share some of the letters she wrote Andrew during that time — and she really did let him know how she was feeling. 

"I am agonizingly jealous of your other women," read one note to him. "None will care about you like I do. None will ever love you as much. Give me another chance, Andy," pleaded another. Still another saw Stewart allude to having told him that she wanted to burn their home down, since he no longer saw it as his, despite all the years and efforts they'd put into it. 

Unfortunately for Martha, her attempts at persuading Andrew to give their marriage another shot didn't work out. In fact, he seemed to have little remorse over his affair with her assistant — so much so that he wed the former assistant after his divorce from Martha came through. At some point, they split up, and now Andrew is married to Shyla Nelson Stewart. Notably, in the wake of Martha's revelations in the Netflix documentary, Shyla made a point of responding. Taking to Facebook, she made a pretty damning claim against Martha. "Prior to this happy chapter of his life, Andy had some dark ones, including a painful and abusive marriage to Martha (as in, Martha Stewart), which ended almost 40 years ago," she wrote. Yikes. Nevertheless, she wished Martha the best.

Whether or not she wanted the divorce, Martha Stewart eventually moved on, and she did so with billionaire software developer (and inventor of Microsoft Word), Charles Simonyi. For a long time, they bonded over being high achievers. Simonyi also stayed with Stewart in spite of her time in prison. However, that's not to say he was the most supportive of her during that time. After all, as she shared in "Martha," he only went to visit her once, and he didn't correspond with her much, either. "I don't think he liked hanging out with somebody in jail. He was out on his boat, floating around the world," she mused. 

Simonyi did send his private plane to fetch Stewart after her release (though notably, he wasn't there in person). However, Stewart wasn't quite the same once she came out of prison. By her own account, she was not as "exciting" as she'd been prior, and that ended up impacting their relationship. Even so, she couldn't have seen what was coming. 

Stewart recounted that she had been in bed with Simonyi when he dropped a major bombshell on her. "He said, 'You know, Martha, I'm going to get married.' He said, 'I'm going to get married to Lisa.' I said, 'Lisa who?' I mean, he hadn't told me a word. 'And by the way, her parents don't want me to ever speak to you again,'" she recounted. Understandably, Stewart was blown away — and years later, she's still shocked by how everything ended. "How can a man who spent 15 years with me just do that? What a stupid thing to do to someone that you actually cared about," she said. She's not wrong. Simonyi and Lisa Persdotter are still married today.

Even though Martha Stewart was never married to Charles Simonyi, she does see their relationship as a marriage of sorts. Case in point: she referred to it in "Martha" as her "second 'divorce.'"

As for her love life outside of her two long-term relationships, Stewart did have a few flings. For one, there was Anthony Hopkins. It's not clear how long they were together, but some may be aware that Stewart dumped Hopkins over his iconic role in "The Silence of the Lambs." As she revealed in a 2022 episode of "The Ellen DeGeneres Show," "I have a very big, scary house in Maine that's way by itself on 100 acres in the forest, and I couldn't even imagine taking Anthony Hopkins there. I couldn't. 'Cause all I could think of was him eating ... you know." Fair enough! Other than Hopkins, Stewart also revealed back in 2021 on her eponymous website that she'd been in a brief relationship with billionaire former owner of The New York Daily News, Mortimer Zuckerman. He'd been in attendance at her 50th birthday party, so perhaps it seemed promising at the time. However, Stewart emphasized that they weren't together long, referring to him as "a one-time boyfriend."

In the time since her split from Simonyi, Stewart hasn't had another public relationship. Granted, she did share with Haute Living in 2014 that she would love to change that. "I'm looking for a partner ... I'd love to have a more regular male companion," she said at the time. More than a decade on, perhaps she has found one, and she's just doing what she can to avoid scandal in her romantic life. Given all she's been through, we wouldn't be surprised.