“Bethenny loved him a great deal but it was an unusual relationship,” the source tells PEOPLE about the 51-year-old New York City banker who died of a suspected overdose on Friday.
“They were on and off. It was unconventional and not always exclusive. They would be together and then not,” the insider says. “Sometimes these traditional relationships aren’t the best thing for everybody.”
The Real Housewives of New York City star and Shields, who had been friends for 30 years, began dating in 2016, several months after he separated from wife Jill and three years after the Skinnygirl mogul filed for divorce from ex-husband Jason Hoppy, with whom she shares 8-year-old daughter Bryn.
“Dennis was a steadying rock for Bethenny. He was very mild-mannered and she is like a force of nature but she needed that in him,” the source says.
But Frankel did not want to label her relationship status with Shields, in fact, she preferred it to be a “totally gray” area.
“With Bethenny, it did not have to be black or white. Sometimes they felt like being together and the next week they’d be traveling and take a break. It wasn’t conventional at all,” the source says, adding, “They were both older and had been through marriage.”
Despite their on-again, off-again courtship, Frankel and Shields were each other’s confidants.
“They were always in each other’s lives whether they are officially together or not. Even when they are not together, they don’t sit and define it; it’s just unconventional. They stopped declaring it one thing or another,” the source shares.
From a contentious divorce battle to raising her daughter Bryn and growing her business empire, Frankel has had a full plate these past few years.
“She’s a lot to handle,” the insider says about Frankel.
“She has so much going on and he did too, and trying to make these two very busy people make their lives work can be complicated,” the source shares, adding that Shields did “not seek out the spotlight” though he appeared on a few episodes of the current season of RHONY.
Shields, who was a parent to four children, was also a father figure to Frankel’s daughter Bryn.
“The real tragedy is Bryn. She really loved him. And he was like a second father,” the source says. “Bethenny is a great mom too. And seeing them together tells you how close they are.”
Following news of his death, Shields’ estranged wife Jill, who he was married to for 26 years, told PEOPLE he was the “love of her life.”
“We are all heartbroken. 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,” she said.