Bethenny Frankel and Dennis Shields Reportedly Got Engaged Months Before His Death

Real Housewives of New York star Bethenny Frankel and the late Dennis Shields reportedly got engaged four months before his death, sources told Us Weekly.

One source told the magazine that Shields bought a ring and the two kept their engagement a secret.

“They were very back and fourth,” the source said of the couple, adding that they were “definitely making plans to move forward with things and trying to make it work.”

“Dennis really loved her,” the insider added.

Another source said Shields, 51, and Frankel, 47, “talked about engagement a lot” in the past year.

A friend told PEOPLE about Shields’ proposal, but said Frankel did not wear the ring Shields bought.

“He proposed to her with a ring in April. She wasn’t wearing the ring,” the friend told PEOPLE. “There were some hurdles to overcome before she could make that level of a commitment. She loved him. He’s her family and her best friend and her confidante. Her partner and her business partner.”

The friend continued, “She didn’t say no. She would have loved to have married him, but there were some hurdles to overcome first.”

Shields and Frankel were friends for nearly three decades. Shields’ estranged wife, Jill Shields, was high school friends with Frankel. The two started dating an on-again, off-again relationship in 2016, around the time Frankel was finalizing her divorce from her second husband, Jason Hoppy.

Frankel attended Shields’ funeral on Long Island Monday. She also shared a photo of Shields on Instagram, showing him laying on a bed with her dog Cookie, who died in October 2017.

“Rest In Peace my sweet babies who gave me endless unconditional love. #nowandforever,” Frankel wrote.

Jill Shields issued a statement on Friday, telling PEOPLE, “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.”

Shields was found dead in his Trump Tower apartment Friday morning from a suspected overdose. He woke up Friday morning feeling like he overdosed on prescription pills and asked an assistant to get him a dose of Narcan, a drug used to reverse an opioid overdose in emergencies. The drug was reportedly administered, but he lost consciousness and died moments later. Sources told Page Six he overdosed on OxyContin.

In last week’s episode of RHONY, Frankel opened up about her relationship with Shields.

“I didn’t say this to Dennis, but in my own mind I said 90 days. I’m not saying a word to Dennis for 90 days,” Frankel told Dorinda Medley, notes PEOPLE. “It’s a really hard thing to realize that someone you love doesn’t mean they’re the right person. I wish he was.”

Shields was the founder of Esquire Bank and Yield Street, and the CEO of pre-settlement funding firm LawCash.

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