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Secrets & Scandals That Rocked Bethenny & Dead Boyfriend Dennis Shields' Relationship

bethenny frankel boyfriend dead prescription pills overdose on off relationship
Source: INSTAR/MEGA

Feb. 25 2019, Updated 11:49 a.m. ET

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Bethenny Frankel’s on-again, off-again boyfriend passed away on Friday after he was discovered dead at his Trump Tower apartment of a suspected overdose, and now RadarOnline.com can exclusively reveal the on-again, off-again couple's rocky past. RHONY star Frankel, 47, and Shields, 51, first started dating back in late 2015, but called off their relationship sometime before May of 2016. They had been up and down ever since. The relationship took off on a rocky start after it was revealed Shields, who served as the executive chairman of the board of New York’s Esquire Bank, was STILL married to Frankel’s longtime friend from high school when they started dating! Click through Radar's gallery for more!

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bethenny frankel boyfriend dead prescription pills overdose on off relationship
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According to reports, Shields' untimely death came after he believed he was overdosing on prescription pills at 9 a.m. and allegedly asked his assistant to administer Narcan, but he lost consciousness before it was able to kick in and was pronounced dead soon thereafter.

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But before his tragic passing, Shields made headlines for being Frankel's new arm candy, however, the relationship wasn't easy, in part due to the fact he was still married to someone she knew. “Bethenny and Dennis’ soon-to-be-ex-wife have a long history. He’s had feelings for Bethenny for a long time.”

bethenny frankel boyfriend dead prescription pills overdose on off relationship
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Frankel also banned Shields from appearing alongside her on RHONY. “She refused to film with Dennis, saying that she wanted to keep her personal life separate from the show." As a result, her co-stars were blasting her efforts to keep the drama under wraps — creating even more pressure on the newly formed relationship. “It’s a reality show. What does Bethenny think she’s doing?” Ramona Singer and Dorinda Medley sniped about Frankel hiding her relationship.

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bethenny frankel boyfriend dead prescription pills overdose on off relationship
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But things were looking up for the couple despite all the setbacks. Reports in summer 2016 suggested the Skinnygirl mogul had been house-hunting with her new man in Tribeca, and they even looked into purchasing a $30 million penthouse.

bethenny frankel boyfriend dead prescription pills overdose on off relationship
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But that flame was quickly put out. Months late, the Big Apple-based banker was so keen on the reality star he wanted to pop the question, but she turned him down. “Bethenny and Dennis continue their ongoing love saga of being in each other’s lives,” a source spilled to Radar at the time, but unlucky for Shields, “she just doesn’t want to put a label on their relationship.”

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bethenny frankel boyfriend dead prescription pills overdose on off relationship
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Although Shields served as a pillar of support for the reality star during her custody war with ex Jason Hoppy, the tumultuous time still took a toll on their romance Just a few months ago, sources told Radar exclusively Frankel was "still going through absolute hell” with Hoppy, as she tries to get sole custody of their 7-year-old daughter, Bryn, putting a damper on her love life with Dennis. As a result, informants revealed: “They do fight, and will go a few days without talking, but it typically doesn’t last that long.”

bethenny frankel boyfriend dead prescription pills overdose on off relationship
Source: MEGA

Amid all the drama, pals told Radar Frankel just did not have enough room on her plate for marriage, so she turned down Shields’ desires to tie the knot. “It’s just not the right time for Bethenny to even consider marriage, and she doesn’t know if she ever wants to go down that road again.”

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bethenny frankel boyfriend dead prescription pills overdose on off relationship
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To make matters worse, Radar exclusively revealed in 2016 Shields had been involved in multiple lawsuits. According to New York Supreme Court documents obtained by Radar, the New York-based banker and his estranged wife Jill sued another couple and their attorney in 1995 for refusing to refund their $75,000 deposit on the pair’s Long Island property.

bethenny frankel boyfriend dead prescription pills overdose on off relationship
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Years later, in 2009, Dennis and Jill filed a petition against a Long Island town to reduce their property’s full market value to $1.8 million from $2.5 million in a challenge to tax assessments. However, the petition was eventually dismissed from court.

bethenny frankel boyfriend dead prescription pills overdose on off relationship
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Police confirmed Shields' passing to Radar: "On Friday, August 10,2018, at approximately 0919 hours, police responded to a 911 call of an aided male inside of 721 5th Avenue. Upon arrival, officers discovered an unconscious male at the location. EMS responded and pronounced the male deceased. The NYC Medical Examiner will determine the cause of death and the investigation is ongoing. We pay for juicy info! Do you have a story for RadarOnline.com? Email us at tips@radaronline.com, or call us at (866) ON-RADAR (667-2327) any time, day or night.

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