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Unraveling the Ups and Downs of Martha Stewart’s Love Life

A Look At Martha Stewart's Tragic Relationship History

Those who watched the Netflix show “Martha” are likely aware that Martha Stewart’s romantic past is far from idyllic. It features many heart-wrenching moments, and Martha herself has openly shared her feelings of devastation following significant heartbreaks. Interestingly, she also displays a level of detachment regarding her relationships.

During a candid moment in the documentary, she revealed that she has never been in a relationship where she openly discussed her feelings with her partner. Without hesitation, she stated that this kind of dialogue does not appeal to her. Her nonchalant attitude suggests that she may not have pursued many serious connections because of this outlook.

However, it would be misleading to say Martha has never had serious relationships. In fact, she was married to Andrew Stewart for nearly 30 years and later had a prominent romance with Charles Simonyi, both of which concluded unsuccessfully for her.

Martha married her husband against her father’s wishes

In the documentary, Martha recounted falling deeply in love with Andrew Stewart during her college years, largely due to his kindness—a stark contrast to her incredibly strict father. She shared a moment from their engagement when her father reacted violently upon learning of her intentions. Despite the slap and his bigoted disapproval of Andrew’s Jewish heritage, Martha proceeded to marry him.

Even from the start, the relationship faced challenges. During part of their honeymoon, Martha had a striking experience at the Cathedral of Santa Maria del Fiore. Moved by the beauty of the cathedral, she shared an impulsive kiss with a stranger but did not view it as unfaithfulness, seeing it as a mere emotional moment.

Both Andrew and Martha Stewart had affairs

Martha’s encounter at the Duomo was only one of the complexities in her marriage. She openly discussed Andrew’s numerous affairs following their relocation to Westport, and expressed regret for not ending their relationship sooner upon realizing his unfaithfulness. She offered a stern warning to young women, advocating for self-respect if faced with infidelity.

In an unexpected twist, Martha also confessed to having a brief affair during her time as a stockbroker, which she regarded as insignificant and not worthy of affecting any marriage. Although she claimed she never told Andrew about it, the documentary hinted that Andrew’s affairs began after her revelation.

The insights in “Martha” weren’t the first look into the couple’s infidelities; previous accounts indicated variations in Martha’s Duomo story, leaving some doubt about the circumstances surrounding her kiss with the stranger.

Martha Stewart’s Painful Split from Andrew Stewart

Despite the turmoil, Martha Stewart never expected her marriage to Andrew Stewart to end. Consequently, she was left heartbroken when it did. Although she initially joked about her feelings, she later admitted that discussing her efforts to salvage the marriage was tough, revealing some heartfelt letters she had written to Andrew during that chaotic time.

In one letter, she expressed, “I am agonizingly jealous of your other women,” and in another, she pleaded, “Give me another chance, Andy.” She even hinted at her drastic feelings about their home, stating she wanted to “burn it down” since he no longer viewed it as their shared space.

Unfortunately, her attempts to reignite their marriage were in vain. Andrew seemed untroubled by his affair with her assistant, later marrying her soon after their divorce. Following revelations from Martha’s Netflix documentary, Andrew’s current wife, Shyla, publicly commented, implying that their previous marriage had been challenging and voicing her support for Martha nonetheless.

Abrupt End to Martha’s Relationship with Charles Simonyi

After her marriage ended, Martha Stewart began a relationship with billionaire Charles Simonyi, the creator of Microsoft Word. They connected over their drive for success, and he remained with her during her prison sentence, albeit offering minimal support, visiting only once. Stewart noted that he was preoccupied with his yacht adventures during her incarceration.

Though Simonyi sent a private plane for Stewart post-release, he wasn’t there to welcome her. Their relationship took a turn after her release, as she felt she lacked the excitement she once had. In a shocking moment, while they were together, Simonyi announced his engagement to another woman, leaving Stewart bewildered by his abrupt decision after 15 years together.

Stunned, she reflected on how he could end things so cavalierly with someone he cared for, and now, he remains married to Lisa Persdotter.

Martha’s Brief Romantic Encounters

While not married to Charles Simonyi, Martha viewed their bond as significant, dubbing it her “second ‘divorce.'” Beyond her long-term commitments, Martha has ventured into a few short flings, including a romance with actor Anthony Hopkins, whom she reportedly ended things with due to his well-known chilling role in “The Silence of the Lambs.”

In addition, she dated Mortimer Zuckerman briefly, describing him as a “one-time boyfriend” despite his attendance at her 50th birthday celebration.

Since separating from Simonyi, Martha has kept her romantic life private though she expressed a desire for companionship a decade ago. Now, possibly content with her current status, she might be avoiding the limelight in her personal life, which—aided by her past experiences—seems entirely reasonable.

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