Dennis Shields & Bethenny Frankel — PICS

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August 10, 2018 1:56PM EDT

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Dennis Shields & Bethenny Frankel talk in New Yoek

Dennis Shields & Bethenny Frankel talk in New Yoek — Bethenny Frankel and Dennis Shields met nearly 20 years ago, when he was dating one of Bethenny’s high school friends. After losing touch, they reconnected in 2016 and soon started dating. He then proposed to Bethenny in April 2018, but she didn’t give him a definitive answer on whether or not she wanted to marry him. Instead, she told him things were on “ice” until some “conditions” had been met and “changes” were made. She eventually broke things off a few months later, and after a few days went by, Dennis was found dead in his Trump Tower apartment from a suspected overdose. Due to religious reasons, an autopsy was never done, so his cause of death was listed as “undetermined”. In the ‘RHONY’ episode that aired in March of 2019, Bethenny explained ““It’s funny because he said to me, ‘Did you say yes?’ And I said, ‘Well, I love you and I can’t believe you did this but we have to talk about some conditions and some terms and how things are going to change’ — issues I’ve had with partnership and consistency,” Bethenny remembered about the moment. “It was all very complicated and it wasn’t what a natural engagement should be. So our engagement was on ice.”

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Dennis Shields & Bethenny Frankel carrying gifts

Dennis Shields & Bethenny Frankel carrying gifts — Dennis Shields and Bethenny Frankel appeared to be happy while together. In this photo, Dennis can be seen holding a gift bag while she smiles for the cameras and holds a hand towel. (REX/Shutterstock)

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Dennis Shields & Bethenny Frankel leaving a building

Dennis Shields & Bethenny Frankel leaving a building — The April 10, 2019 episode of The Real Housewives of New York City was a heartbreaking one, as Bethenny Frankel, 48, confided in Dorinda Medley and revealed that she made a huge mistake by going to see A Star Is Born while in Boston. And that’s because the addiction plotline, during which Bradley Cooper‘s character battles addiction, triggered memories of her late ex, Dennis Shields, who died from a suspected overdose in August 2018.

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Dennis Shields & Bethenny Frankel looking happy

Dennis Shields & Bethenny Frankel looking happy — “Last night I went to see A Star Is Born,” Bethenny told Dorinda after arriving at her co-star’s Berkshires home for the cast’s annual girls’ trip. “I cried, you don’t understand, at the end — I didn’t know it was about pill addiction.”

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Dennis Shields & Bethenny Frankel walk in NYC

Dennis Shields & Bethenny Frankel walk in NYC — Bethenny said she could barely get through the ending of the Lady Gaga-led movie when she saw Jackson Maine (Bradley Cooper), die by suicide after a relapse. “The whole thing, it killed me,” Bethenny said, as her eyes started getting watery. “The guy was like, he loved her so much. He died for her. … I thought about all the texts I sent to him that week when I said ‘Look, I can’t do this anymore’ and he said, ‘Babe, it’s so rough, I miss you, I love you.’ I cried for like an hour last night! I was freaking out. I sat by myself in the movie theater for an hour! Going to Boston and seeing A Star Is Born could be one of the most stupid things I’ve ever done in my life.”

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Dennis Shields & Bethenny Frankel smile for the paparazzi

Dennis Shields & Bethenny Frankel smile for the paparazzi — Dorinda, who lost her own husband a number of years ago, understood what Bethenny was going through, so she offered her some advice. “Remember what I said? You were never going to move on in a healthy relationship,” the 54-year-old reminded Bethenny. “This was his journey,. Period. Everything has a beginning, middle and end and it’s not for you to determine. You are now living your best life with your daughter. You can always call me. I have been through a similar thing, and I get it. It’s a lonely but growing thing.”

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