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Was Bethenny Frankel's Relationship With The Late Dennis Shields Unstable?

The shocking apparent drug overdose death of The Real Housewives of New York star Bethenny Frankel's boyfriend is putting scrutiny on their on-again, off-again relationship.

Banker Dennis Shields, 51, was found dead of a suspected overdose on Friday, August 10, 2018 about 9 a.m. in his million-dollar Trump Tower apartment in New York.

The New York Post reported that the businessman —and RHONY guest star — had allegedly overdosed on prescription pills.

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Shields reportedly asked his assistant to administer Narcan, which treats opiate overdoses, when he realized his life was in danger. But it was too late.

Now, a source has told PEOPLE, "Bethenny loved him a great deal but it was an unusual relationship.

"They were on and off. It was unconventional and not always exclusive. They would be together and then not."

As reported, Shields claimed he and Frankel had still been together about four weeks before he did an interview about their romance.

Shields spoke to Mitchell Chadrow for his "Listen Up Show" podcast, which had been recorded on Saturday, August 4, according to The Blast.

"About four weeks ago we were still together," Shields claimed, then continued about his turbulent relationship with Frankel, 47, "I was looking at something on the internet and then all of a sudden I Google her or me and she said, 'What are you doing?' And I said, 'I'm just checking to see how our relationship is doing.' "

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He then laughed.

The banker told host Chadrow that he and Frankel had been friends at first. Shields met the future reality TV star when they were both still in college.

"My ex-wife Jill and her were friends in high school," Shields explained in the recently-surfaced interview. "We remained friends the whole time that I was married…nothing but friends, and then after…I got separated, Bethenny and I started dating and we have been together on and off now for I think it's almost four years."

Dennis Shields

Although Shields said it had been four years, most reports state that Frankel began dating Shields in 2016.

Shields praised Frankel, the mother of daughter Bryn, 8, by her ex, Jason Hoppy, as a "great mother, a great person. She's really, really smart. She's terrific in every way."

According to the PEOPLE report, Shields was Frankel's "rock" and close confidant.

But she didn't exactly want to call him her boyfriend, as they often took breaks in the relationship.

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Because both had suffered broken marriages, Frankel and Shields' situation "wasn't conventional," the PEOPLE source noted.

The banker wasn't too keen on the spotlight, but as fans know, he did appear on a few RHONY episodes with Frankel.

The source told PEOPLE that Shields, who had four kids, was a loving presence in the life of Frankel's daughter Bryn.

"He was like a second father," the insider disclosed.

As reported, the New York City Medical Examiner is "investigating" Shields' death.

His passing sent shockwaves through the reality show's cast and as a source revealed, Bravo has silenced the RHONY ladies in the wake of the news.

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