Martha Stewart Regrets Not Having More Children Or Finding Love Again Post Divorce

Martha Stewart, 82, has built an empire around being the hostess with the mostest. She’s a businesswoman and pop culture icon. According to Investopedia, she is worth around $400 million.

Despite all her career success, Martha has some regrets. She opened up about these in a New York Times interview that was published on April 5, 2024. She wishes she'd had more children. She also wishes she had tried to find love again after her divorce from Andrew Stewart.

Martha studied history and architectural history at Barnard College, Columbia University. It was during this time that she met, fell in love with, and married Andrew at 19 years old. After she graduated in 1963 she modeled for a spell. Many don’t know she went on to be a successful stockbroker on Wall Street.

The stock market crash of 1973 inspired her to change careers. She opened up a catering business with a friend, setting the stage for the persona we know today. It wasn’t easy to make this change in her 40s.

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"Maybe a little uncertainty can help fuel ambition," she mused. "When I left my job on Wall Street, I knew I had to create a career for myself. I became a caterer, catering parties every night."

This shift caused things to sour in her marriage. She and Andrew separated in 1987 and divorced in 1990. "At that time I wasn’t keeping my eye on the home, even though I was known as a homemaker. It wasn’t enough for a marriage," Martha recalled.

Hindsight is always 20/20. Looking back, Martha may have wanted more children but was processing so much. "Maybe I regret not having had more children. Maybe I regret that my marriage ended abruptly. We’d been together 27 years," she went on to say.

It is easy to look at one’s life and wonder what if. Martha can’t help but do this very thing herself. "Maybe I would have liked getting married again. I didn’t, but I don’t mind," she stated. "Still, I’m curious about what could have been."

Alexis was born in 1965 and is now 58 years old. It wasn’t easy growing up in her mother’s shadow. She even wrote a tell-all book about it in 2011, Whateverland: Learning to Live Here.

Martha opened up to People about their close but sometimes tense relationship. “I tried to involve her in everything, but the minute she could leave home and go to boarding school, she did,” she recalled. “Our relationship has always been a difficult mother-daughter relationship. Difficult, but she would do anything for me, and I would do anything for her."

These days, Alexis works as a television host and radio personality. She is a mother of two, whom she welcomed to the world with the help of gestational surrogacy. Jude was born in 2011 and Truman was born the following year.

"I like kids," Martha stated at an event in 2014. "I wish I would have had a lot. I try to see the little kids [grandchildren] at least three or four times a week. Being a grandparent is very important. When I see my daughter smile at the children, it's just heart melting."