Dennis Shields Proposed to Bethenny Frankel Before His Death, but 'There Were Some Hurdles'

Despite their complicated relationship status, Bethenny Frankel and Dennis Shields considered marriage in recent months — and he even gave her an engagement ring.

A friend of the Real Housewives of New York City star tells PEOPLE that the couple were discussing the possibility of marriage this past spring.

“He proposed to her with a ring in April. She didn’t wear the ring because they had some things to work out first,” the friend says. “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.”

Still, Frankel, 47, kept the news a secret. “Very few people knew about the proposal,” the friend says. “He’s proposed before — but never with a ring.”

Her answer?

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

In the wake of his death, “Bethenny is devastated,” the friend says.

Shields was found dead in his Trump Tower apartment on Friday. He was 51. The NYPD is investigating his death as a possible overdose. According to the New York Post, the banker asked his assistant to give him Narcan, an emergency medication intended to reverse the effects of a narcotic overdose, but he lost consciousness before the medication could take effect.

Perhaps complicating his future with Frankel, Shields was still legally married to his estranged wife Jill, who referred to him as “the love of my life” in a statement to PEOPLE after his death.

Frankel and Shields began dating in 2016 — three years after the Skinnygirl founder filed for divorce from ex-husband Jason Hoppy, with whom she shares 8-year-old daughter Bryn. But they first met about 28 years ago when he dated (and later married) Jill, one of her high school friends. They began seeing each other several months after he separated from his wife.

But they dated on and off for years, and on last week’s episode of RHONY, Frankel suggested they were taking another break, though they always remained close friends through their ups and downs.

“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 friend Dorinda Medley. “It’s a really hard thing to realize that someone you love doesn’t mean they’re the right person. I wish he was.”

On Monday, Frankel posted an Instagram of Shields cuddling with her beloved dog Cookie, who died in October at the age of 17. “Rest In Peace my sweet babies who gave me endless unconditional love. #nowandforever,” she captioned the intimate photo. And she was photographed looking heartbroken while attending Shields’ funeral on Long Island.

Frankel’s friend tells PEOPLE it’s unclear whether she and Shields were officially together leading up to his death. Still, their feelings were undeniable.

“She talked to him this past week. He loved her and she loved him,” the friend says. “She would have loved to have married him, but they were still working through their issues. She wanted to make it work.”