The 51-year-old businessman was found dead in his Trump Tower apartment of a suspected overdose in August
In a preview for next week’s episode of The Real Housewives of New York City, Frankel, 48, revealed to costar Dorinda Medley that Shields, who died in August of a suspected overdose, had asked her to marry him. He was 51.
“He proposed on April 25… I didn’t tell anybody that,” Frankel told Medley, 54, before showing her the massive ring.
“I didn’t know that,” Medley said in response.
“We had our own private engagement and our own private, like, ‘Oh my God, we’re going to do this,” Frankel said back.
When asked if her daughter with ex-husband Jason Hoppy knew, the Skinnygirl mogul said: “He bought Bryn a ring, too.”
The reveal brought both Frankel and Medley, who lost her husband Richard H. Medley in 2011, to tears.
“I loved him so much and we were a family and my daughter was close with him and I knew him for so many years,” Frankel told Medley.
On the season 11 premiere of the Bravo franchise, Frankel got teary-eyed about Shields and his effect on Bryn.
As tough as it was to lose Shields, seeing how it affected Bryn was “another sucker punch,” Frankel said. She recalled to her friends how Bryn asked if Shields still had a phone number, and then texted him a message: “Hi Dennis, how are you doing today? We miss you. Kiss. I and [dogs] Biggie Smalls miss you as well. From, Bryn.”
“She said, ‘I miss you. I wish you were here today,’” Bethenny said, breaking into tears. “It’s so sad.”
In August, Frankel spoke to PEOPLE about her loss. “It’s been very, very hard, I love him very much,” she said at the launch of her SkinnyGirl Jeans line. “He’s very much a part of me and he’s very much a part of this [launch]. He was very involved in my endeavors.”
“He would be so excited. I can hear him saying, ‘How many did you sell?’ and ‘I can’t believe you sold out.’ And he would be checking the numbers and checking the website,” she continued. “He’s here and I just know he would be so proud and a cheerleader.”
Of the grieving process, Frankel said: “It’s like [Hurricane] Florence, it’s a storm and you must go through it. It’s not one of these things you can avoid and you have to go through it and deal with it and hopefully, you come out stronger on the other side.”
Frankel and Shields began dating in 2016 — three years after she filed for divorce from Hoppy.
They first met nearly 30 years ago when he dated (and later married) Jill Shields, one of Frankel’s high school friends. Though Frankel did not stay in touch with her classmate (“We’ve spoken three times in 25 years,” she previously told PEOPLE), Frankel and Shields shared other mutual pals.
As sad as the loss has been, Frankel has found love again. She’s currently dating real estate developer and film producer Paul Bernon. The two made their relationship Instagram-official in December when Frankel shared two photos of the couple celebrating Christmas together in the Dominican Republic. Frankel and Bernon went on to ring in the New Year together in Mexico, joined by Bryn and his two kids.
The Real Housewives of New York City airs Wednesdays (9 p.m. ET) on Bravo.