Bethenny Frankel's on-off boyfriend, businessman Dennis Shields, died the morning of Aug. 10 from a suspected opioid overdose in his Trump Tower apartment in New York City, multiple outlets reported.

Page Six is now reporting that on the Aug. 8 episode of "The Real Housewives of New York City" that aired two days earlier, Bethenny, 47, regretfully talked about how Dennis, 51 -- to whom she's been romantically linked publicly since 2016 following nearly 30 years of friendship -- just wasn't the right man for her.


Friends are speculating, Page Six claims, that Bethenny's confession could have sparked what it calls "a deadly tailspin." The New York Post cited police sources when it reported that Dennis -- who some reports claim was taking OxyContin for back pain -- died around 9 a.m. Friday after asking his assistant to administer Narcan, which can reverse the effects of an opioid overdose.

A friend summed up Bethenny's comments -- which she shared while telling fellow "RHONY" star Dorinda Medley that she couldn't live with Dennis -- like this: "She [basically] said, 'I love him, but I could never marry him."

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Dennis had nice things to say about Bethenny when he was asked about her on the Aug. 5 episode of the business podcast the "Listen Up Show with Mitchell Chadrow," Page Six reported. "We remained friends the whole time that I was married -- nothing but friends," he explained. "And then right after Jill [who was one of Bethenny's high school friends] and I got separated, Bethenny and I started dating, and we've been together on and off now for I think it was almost four years. That's what she told me ... But we do break up a lot."

It's believed that Bethenny and Dennis were "off" at the time of his death.

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In May, Bethenny talked about their unconventional romance and friendship while visiting Steve Harvey's talk show. "I've been with someone on and off for years. It's like a partnership where if we're not being teammates and it's not working and one man is down, then the other man is down," she said, as reported by People magazine, which has described their relationship as "complex."

"We're trying to really kind of be good partners and be good teammates and I think relationships oddly are -- and this sounds cold -- but a little bit like business. If both people aren't happy about it but slightly uncomfortable and giving up something or giving in [to] something, it doesn't work. So both partners have to say, 'All right, I'm in it for this,'" she continued, adding, "And I think we might be at that point, believe it or not. I haven't said that to anyone yet."

E! News reported that Bethenny, who has yet to speak publicly about Dennis' death, is devastated. "She's heartbroken," said the source.