By Alexandra Whittaker
Updated Aug 14, 2018 @ 10:30 am

Real Housewives of New York star Bethenny Frankel was devastated by the unexpected death of her on-off boyfriend Dennis Shields, who was found dead in his Trump Tower apartment on Friday of a suspected overdose. He was 51.

On Tuesday, a new development only added to the heartbreak. According to People's sources, marriage may have been on the horizon for the couple before Shields passed away.

“He proposed to her with a ring in April. She wasn’t wearing the ring,” the friend said. “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.”

Though Frankel chose not to wear the ring, that didn't necessarily mean she outright rejected his proposal.

Bethenny Frankel and Dennis Shields lead
Credit: Alessio Botticelli

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

The proposal was purposely kept secret, but it turns out this wasn't the first time he had asked for her hand. “Very few people knew about the proposal,” the friend said. “He’s proposed before — but never with a ring.”

Now that Shields has passed away, the friend said Frankel is understandably "devastated." Frankel broke her silence on the ordeal on Monday with an Instagram of Shields alongside her beloved late dog Cookie, who died in October.

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