Just days before Dennis Shields died, Real Housewives of New York City star Bethenny Frankel reportedly said she think she could marry him.
Friends told Page Six that Frankel told them he was not "Mr. Right" two days before his death.
"She [basically] said, 'I love him, but I could never marry him,'" one friend told Page Six.
Shields, a 51-year-old banker, was reportedly found dead Friday morning in his Trump Tower apartment from an apparent overdose.
According to reports, he thought he overdosed on some prescription pills and asked an assistant to get a dose of Narcan, a drug used to reverse the effects of an opioid overdose. Although the drug was administered, he reportedly lost consciousness before it took effect and he died moments later.
Late Friday, the New York City Chief Medical Examiner's Office confirmed that a body was found at Trump Tower, but did not confirm the victim's identity. An official cause of death will not be determined until after the investigation is completed.
However, Shields' estranged wife, Jill Shields, confirmed his death in a statement to PEOPLE Magazine Friday. The couple were married for 26 years and split in 2016.
"We are all heartbroken," Jill Shields said. "Dennis was, and will always be, the love of my life. His spirit lives on in our children. Please respect our family's privacy at this time."
Shields and Frankel had known each other for almost three decades because Jill Shields was a high school friend of hers. The two began an on-again, off-again relationship in 2016, after Frankel's divorce from her second husband, Jason Hoppy, was finalized.
In an interview for the Listen Up Podcast days before his death, Shields said they were still together as of "about four weeks ago." He jokingly said he needed to look up Frankel on the Internet to find updates on the their relationship.
"She's great. She's a great mother," Shields said of Frankel on the podcast. "She is terrific in every way... But we do break up a lot."
A witness told Page Six that Shields was seen in Manhattan, enjoying a solo dinner at a trendy new restaurant. "He looked so happy and healthy and vibrant on Tuesday," the witness said.
After Shields' death, Real Housewives of New York fans sent their condolences to Shields' family, as did former RHONY star Carole Radziwill.
"I just heard the sad news about Dennis. He was a good man," Radziwill tweeted on Friday. "My condolences to all his family and friends. So tragic."
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