When Martha Stewart Lost Her Virginity
Martha Stewart—then still Martha Kostyra—lost her virginity when she was 19, to her future husband Andrew Stewart, a student at Yale Law School.
“He was very aggressive,” the lifestyle mogul said in the 2024 Netflix documentary Martha, “and I liked it.”
Martha Stewart Kissed Another Man—on Her Honeymoon
It wasn’t a harbinger of good things to come, but Martha maintained that kissing another man while she and Andrew were honeymooning in Europe after their 1961 nuptials wasn’t that big a deal.
“It was neither naughty nor unfaithful,” she said in Martha of smooching the stranger at a cathedral on Easter eve in Florence, Italy. “It was just emotional, of the moment. That’s how I looked at it. And it was exciting. I wish we could all experience such an evening.”
Martha Stewart Cheated on Husband Andrew Stewart
Martha admitted in the documentary to a “very brief affair” with “a very attractive Irish man” during her time working as a stockbroker in the late 1960s.
“I would have never broken up a marriage for it,” she said. “It was nothing. It was like the kiss in the cathedral.”
She insinuated that Andrew was repeatedly unfaithful, despite her ex-husband maintaining he didn’t cheat until she confessed her infidelity.
“I didn’t go run off with people. He was running off with people,” she said. “I always said I was a swan and like all swans, they are monogamous.”
Being a Mom Wasn’t a Natural Fit for Martha Stewart
Martha had to work at honing her maternal instincts when her daughter Alexis Stewart was born in 1965.
“Back then, everybody was having babies so young,” she reflected in Martha. “That was sort of the style and the habit. I thought it was a natural thing, and it turns out it’s not at all nature to be a mother.”
While she and Alexis remain close, Martha told People in 2020, “I tried to involve her in everything, but the minute she could leave home and go to boarding school, she did. 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."
Martha Stewart Spent Time in Solitary
Martha infamously served five months at FPC Alderson after being convicted in 2004 of conspiracy, obstruction and lying to federal investigators in connection with an insider trading case.
At one point she was punished for touching a female guard’s “big silver key chain” after complimenting how nice the guard looked, as she shared in Martha, having momentarily forgotten the prison rules.
She ended up “dragged into solitary for ‘touching an officer,’” Martha said. “No food or water for a day. This was ‘Camp Cupcake,’ remember?”
Martha Stewart’s Thoughts on Hosting a Talk Show
Upon her release in March 2005, as Martha put it in the doc, she “had to climb out of a f--king hole”—and daytime TV seemed like a step in that direction.
But while she’s been the face of countless endeavors over the years, onscreen and off, hosting Martha for seven seasons, she said, “was more like prison than being at Alderson.”
Did Martha Stewart Have a Facelift?
Martha said on a February 2024 episode of her eponymous podcast that she never had a facelift, but her dermatologist Dr. Daniel Belkin did inject Botox in her neck and along her jawline and put filler in her cheeks and jawline.
Belkin noted that they had also done ultrasound-based skin tightening, and she recalled having a Fraxel laser treatment on her body.
"My décolletage and across my chest looks so good now," Martha told the doctor. "That is a combination of your work and Pilates." She further chalked up her radiant visage to clean eating—her daily green juice ingredients come straight from her garden, naturally—and staying active.
Martha Stewart Enjoys Snoop Dogg’s Contact High
While she didn’t partake herself, Martha felt “fabulous” when her friend and frequent cohost Snoop Dogg smoked weed around her, she shared when he was a guest on the 2022 premiere of her podcast.
“It makes me feel really good," she confessed. "It does not disturb my concentration. In fact, I think it makes it even better and it doesn't make me tired or any of the things people say marijuana does to you. It's fantastic, I think it's great."
The Alcohol Martha Stewart Hadn’t Tasted Since College
Martha loves a craft cocktail, but there’s one spirit that has haunted her since she was a student at Barnard.
“I got so drunk on gin in college,” she told Snoop in 2024 at Food Network's New York City Wine & Food Festival, “that I have not ever had gin since.”
"But," she told her friend, who inevitably entered the alcohol market with the drink he's been linked to for 30 years, "I can’t wait to taste your Gin & Juice!”
Unclear if she did!
Incidentally, though Martha is practically synonymous with white wine, she is not a day drinker.
“I never drink it before dinner, ever," she told The Cut in 2017. "I couldn't function for a second if I had to drink it at lunchtime or something like that."
Why Martha Stewart Doesn’t Wear Underwear
Martha skips wearing underwear in lieu of having her swimsuit on at all times—just in case she feels like taking a dip.
"Bathing suits are my underwear," the 2023 Sports Illustrated Swimsuit Issue cover girl told Page Six in 2024. "I don't wear any of that structured stuff. No tight lace. I don't wear those. I only wear Eres bathing suits under my clothes."
Martha Stewart’s One-Night Stand Confession
On Watch What Happens Live! in 2013, the answer was “yes” when Andy Cohen asked if Martha ever had a one-night stand. She had also sexted, FYI, and her answer to whether she’d ever had a threesome was a smirking “maybe.”