Martha Stewart's Relationship History Is Like a Good Meal — Sometimes It's Better to Dine Alone

Most people will never forget where they were when Sports Illustrated dropped its 2023 swimsuit issue. It's always quite a feast for the eyes but that year, it was a 100-course dinner. This is of course when an 81-year-old Martha Stewart graced its covers looking, with respect, like a snack. Beyond the fact that the photos were stunning, the 2023 edition allowed us to imagine a world where anyone is allowed to wear a bathing suit in a magazine. They said it couldn't be done.

After it dropped, Martha revealed that her DM's had gotten a little more sassy than usual. Despite that, she coyly told Entertainment Tonight that, "You have to make time for certain things." What mattered to her was tending to her garden and spending time with her two grandchildren. As far as we know, Martha's priorities haven't shifted, but that doesn't mean she hasn't tended to another garden once upon a time. Let's take a look at Martha Stewart's relationship timeline.

Martha met her first, and only, husband Andrew Stewart when she was 20 years old, per People Magazine. She was studying European history at Barnard College in New York City, when Martha went on a blind date with an "extremely serious" man. Andrew was a 23-year-old Yale law student who swept the young model off her feet. The two were married in 1962 and welcomed their daughter Alexis three years later.

Martha worked on Wall Street as a stockbroker until the family moved to a house in Westport, Conn. in 1972. By then she already knew how to beautifully make every recipe in Julia Childs's Mastering the Art of French Cooking, So Martha started her own catering company. She claims that as her star rose, it created cracks in their marriage. She and Andrew separated in 1987 and divorced in 1990. Nearly 30 years later, Martha would reveal in a Netflix documentary that they both had affairs.

The Netflix documentary, aptly titled Martha, briefly touches on the other significant relationship Martha has been in. Three years after her divorce Martha befriended Charles Simonyi, the man behind Microsoft Word and Excel. He was well on his way to becoming a billionaire, as was Martha, and they both insisted their relationship was only platonic.

They spent far too much time together to remain just friends. In June 1999, they attended a White House dinner together. One month later, the duo was spotted at film producer Joel Silver’s wedding in Venice, per New York Magazine (via People). They carried on like this for years until their relationship was interrupted by Martha's legal woes. In 2004, she spent five months in a federal prison after being found guilty of insider trading. During that time, Charles's communication with Martha was spotty.

After she was released, they remained together until 2008, when Charles suddenly ended things. In the documentary, Martha explained that they were visiting the President of Iceland when Charles turned to her in bed and said, "I'm going to get married ... I'm gonna get married to Lisa." She had no idea who Lisa was but Charles continued to drive the knife even deeper by revealing that his future wife's parents never wanted him to speak to Martha again.

Although Martha and Charles were never married, she referred to that breakup as a second divorce. "I thought that was the most horrible thing a person could do. How can a man, who had spent 15 years with me, just do that?" she asked. Other than Andrew and Charles, Martha has not been in any significant relationships, at least not publicly. She did briefly date actor Anthony Hopkins but said she couldn't separate him from his iconic role as Hannibal Lecter in Silence of the Lambs.