On Thursday, July 7, the entrepreneur, 80, got candid during an appearance on the comedian’s podcast, Dear Chelsea. Stewart admitted that she doesn’t have much of a dating life these days but said she’s had “two mad crushes in the last month.”
“But it turns out, you know, one of them is married to the mother of some friends of mine and I just—he’s so attractive,” she divulged.
In response, Handler, 47, said: “You know, you can’t be a homewrecker,” to which the Bad Moms actress replied she’s “had the opportunity” but hasn’t “taken anybody up on it.”
“And that’s really where—that’s where I meet men. They’re all married to friends of mine or something like that.”
She continued: “It’s very difficult because I think there are certain ages we go through where it’s very tempting because you wanna believe that, ‘Oh, maybe this relationship that they’re in is temporary.’”
Stewart then offered up another solution. “Or maybe they’ll die,” she chuckled. “I always think, ‘Oh, gosh, couldn’t that person just die?’”
Handler quickly questioned: “The wife?”
“Yeah! Not painfully,” Stewart clarified. “Just die … but it hasn’t worked out.”
Later on in the podcast, the mom of one, who shares daughter Alexis Stewart with ex-husband Andrew Stewart, revealed she “tried” online dating.
“I have no idea about dating sites,” Stewart said. “I tried that for a while. I mean, once actually. I went out with three different people, and the algorithm doesn’t fit me. Does it fit you?” she asked Handler.
“Well, I mean, you’re a special situation Martha,” the host told her.
“Yeah, I’m an odd situation,” Stewart acknowledged, before adding: “So are you.”
In December 2021, the multimillionaire spilled secrets about her love life while chatting with Andy Cohen on Watch What Happens Live.
When asked if she was seeing anyone special, Stewart said “no,” before changing her tune. “I shouldn’t say no. I mean yes, but I’m not going to tell you.”
Earlier in the episode, Stewart confessed she was once linked to Larry King, though she didn’t specify what year.
The pair had a meal at Elio’s in New York City, a dinner which Stewart assumed was friendly until King seemingly hinted otherwise.
“I thought we were just talking about journalism etc. etc., and then he sort of got a little amorous,” she recalled of their evening. “Everybody was noticing I was out with Larry King, and Larry King was not my type romantically, if you get what I mean.”
Stewart married Yale-educated Andrew Stewart in 1961. The couple split in 1987 and divorced in 1990. Following their breakup, the Martha Stewart Living Omnimedia founder dated software billionaire Charles Simonyi for 15 years, beginning in 1993. She has not remarried.
