Inside Bethenny Frankel And Jason Hoppy's Troubled Relationship

When The Real Housewives of New York City started, Bethenny Frankel was "the single one" in the group. At the time, she was not only struggling to sell baked goods during an appearance at a local supermarket, but was also very specific when she ordered a "skinny margarita," giving detailed instructions to waiters every time she filmed at a restaurant. Bethenny transitioned from being a particular patron to the mastermind behind the prolific Skinnygirl empire. 

This Bravo starlet was also dating a guy named Jason Colodne throughout Season 1, but by the time the show started filming its second season, these two were dunzo. Fans saw Bethenny cope with that breakup and even go on a blind date, but she didn't have much luck. When Season 3 rolled around, Bethenny had a new Jason in her life: businessman Jason Hoppy. She later found out that she was pregnant, they got engaged, and it really seemed like Bethenny was getting everything she wanted in life. Her years of hard work and creativity paid off (literally) with her business success, she was happy in her new relationship, and excited to start her family. It really did feel like a reality TV fairytale ... for a little bit, anyway.

Unfortunately, Bethenny and Jason 2.0's love didn't last, and their issues became increasingly ugly as the years progressed, with no signs of slowing down any time soon. If you think that RHONY is dramatic, the show has nothing on the post-breakup antics between Bethenny Frankel and Jason Hoppy. 

In 2010, Bethenny Frankel married Jason Hoppy and they welcomed their daughter, Bryn. Two years later, Bethenny told ET, "It brings me great sadness to say that Jason and I are separating." The Skinnygirl mogul said, "We have love and respect for one another and will continue to amicably co-parent our daughter who is and will always remain our first priority." Despite her optimism, their co-parenting dynamic has been far from amicable.

TMZ reported that the former New York Housewife filed for divorce in January 2013. By 2016, Jason's lawyer told ET their split had "finally been resolved" and that he was "thrilled that this chapter of his life is over." However, that chapter didn't actually end. After announcing her second departure from RHONY in August 2019, Bethenny tagged her former co-stars in a tweet and wrote, "To my NY hwives: GO GET EM! I had to go since I'm the only one that is actually married...that's how crazy this ride is. You are all amazing, beautiful and strong. Spread your wings and fly!" 

At the time, Jason's lawyer clarified to Page Six that the duo were "still technically married." Additionally, his attorney claimed, "While Jason has been pushing for years to have the judge sign the divorce judgment, Bethenny's lawyers have objected." In September 2020, nearly eight years after they split, Bethenny shared that they were still married during a Watch What Happens Live episode.

Bethenny Frankel and Jason Hoppy have spent more time breaking up than they did as an actual couple. The former pair have so much drama between them that a psychotherapist decided to quit after a year of seeing them. 

In March 2019, Dr. Rami Mosseri testified that he had been appointed to help the exes peacefully co-parent their daughter, Bryn, per Page Six. He had been a therapist for 15 years and he had only quit twice. "I was able to get through to the mother to some degree," Mosseri said during a custody hearing. "I didn't feel at the time that I was able to get through to the father," he shared, claiming that Jason repeatedly complained about the RHONY OG.

In a July 2015 email, Mosseri wrote, "Dear Bethenny and Jason, I'm afraid that in light of the level of conflict between the two of you, the lack of willingness to compromise ... you will be better off with another [parent coordinator]." In court, Mosseri described Bethenny as "controlling" and slammed Jason for his reluctance to compromise, stating, "I believe he had his own idea of what was in the best interest of his child and stuck to it." R Online reported that Mosseri also called Jason an "extremely angry" person who saw things in "black and white." He went on to allege, "Mr. Hoppy didn't have it in him to find the middle for the sake of the child."

In January 2017, Page Six reported that Bethenny Frankel claimed Jason Hoppy sent her many "aggressive" texts and emails, allegedly writing in one message, "Your definition of harassment is comical. I will continue to communicate with you as I see fit." Jason was subsequently arrested after showing up at daughter Bryn's school and allegedly threatening to "destroy" his ex. He was charged with "aggravated harassment in the first degree, harassment in the second degree, and stalking in the fourth degree."

Prosecutors hit Jason with additional stalking charges that June, according to Page Six. He'd supposedly sent Bethenny more than 160 messages in a timespan of several months, and a judge extended an order of protection, which prevented Jason from having any contact with Bethenny. Jason tried to get the charges dismissed in August 2017, but People reported that his request got denied. 

When Bethenny took the stand in March 2019, she alleged while tearing up in the courtroom, "Jason used FaceTime to taunt me, abuse me, say negative things, laugh at me," adding that he did this twice daily before the judge issued an order of protection (via Page Six). She even recorded a heated call from May 2015 when she was trying to talk to their child. Even though it was Bryn's birthday weekend and Mother's Day, Jason allegedly wouldn't let Bethenny talk to her.

Throughout their divorce proceedings and custody battle, both Bethenny Frankel and Jason Hoppy have accused the other of trash-talking in order to influence their daughter's opinions. In 2013, R Online reported that Bethenny called Jason "trash" in front of then-three-year-old Bryn. The former RHONY star confirmed that she called him "white trash" when she testified in March 2019, according to the Daily Mail. 

However, in a 2014 court appearance, Bethenny claimed that Jason told Bryn, "I'm sorry you have to go with Mommy" (via People). Five years later, she alleged (per Page Six), "He would be reading children's stories and say, 'Mommy would be a great witch." March 2019 saw Bethenny's legal team play recordings of Jason bashing the Skinnygirl mogul during a 2015 phone call with their daughter, in which he appeared to tell Bryn, "I don't know why mommy's making it so difficult." 

Meanwhile, Jason claimed that Bethenny wouldn't let Bryn talk to him. However, Bethenny testified that she got Bryn her own phone so she could communicate with Jason directly. At the time, the Bravo star also alleged that Jason used phone calls as an opportunity to turn Bryn against her, per the Daily Mail. "Phone calls were Jason's new tool in his arsenal to abuse me," Bethenny declared, claiming that those phone conversations were "way worse than the emails and texts" that Jason sent, because "having a child in the car with me, or him, while Jason is abusing me, is bad for Bryn."

Despite their very contentious breakup, Bethenny Frankel and Jason Hoppy continued living together, which the RHONY star described as "brutal, horrendous, [and] excruciating" in 2014. According to People, Bethenny claimed in court, "He would not let me be alone with Bryn in the apartment." Adding that Jason would "stare at [her] with a menacing face," she alleged that he'd climb into the bed if Bethenny was laying with Bryn. 

In addition to Bethenny accusing Jason of locking her dog, Cookie, in their storage unit, she claimed that he left once Cookie at a dog hotel, but refused to share Cookie's whereabouts for hours. Bethenny eventually "cracked" and got her own place, and Jason moved out of the apartment in July 2016. Even so, Bethenny continued to spill the tea about their previous living arrangement, revealing in their March 2019 custody hearing (via People), "I had a padlock on my room to protect myself." 

Bethenny described their apartment as "a torture chamber," alleging that Jason "would blast the remote as high as possible" and "leave negative press" clippings about her on the counter: "I would see it and throw it in the garbage, and the next day ... he would take it out of garbage and put it there." Bethenny also claimed that, among other things, Jason would intentionally leave "rotting food" in the fridge, let dishes pile up, and slam doors. She further alleged, "He would go to the bathroom in the toilets and wouldn't flush them."

A week after Bethenny Frankel's ex, Dennis Shields, was found dead in August 2018, Page Six reported that Jason Hoppy questioned the RHONY star's mothering in court. "It was reported that [Shields] died of an Oxycodone overdose," his lawyer stated. "Our concern is while his death is very sad this raises serious concerns about Ms. Frankel's parental judgment." Noting that "Shields spent a great deal of time with Bryn and even cared for Bryn at times when Ms. Frankel wasn't around," the attorney shared "concerns" that Bethenny "may have some type of substance abuse problems" and asked for drug testing. 

In response, the judge said, "Now you're throwing grenades across the table." The judge denied the drug testing request that October, telling Jason, "There was a tragedy which I think you're trying to exploit to embarrass Ms. Frankel." The judge also questioned the "timing" since Jason asked for a drug test after Bethenny's request for a custody trial had been granted.

According to People, an autopsy wasn't performed due to "religious objection," and, as a result, Dennis' cause of death was deemed "undetermined." Bethenny testified that she didn't know if he had an opioid addiction, but she "assumed" he took medication for a back injury. In response to Jason's claims about Bryn's relationship with Dennis, Bethenny said Dennis was very busy with his children, work, and other commitments, maintaining that Bryn spent "less time than [she] did" with Dennis.

In May 2019, Jason Hoppy questioned Bethenny Frankel's social media usage, specifically in reference to a controversial Instagram Story the RHONY star posted in October 2017. The videos featured a tearful Frankel, her dog, Cookie (who was dying from a seizure), and then-seven-year-old daughter Bryn's voice in the background.

"When something notable or serious happens in your life, you immediately post to social media," Jason's lawyer told Bethenny, before questioning her for involving Bryn and asking whether it was "appropriate parenting behavior." The Bravo star defended how she used social media, claiming that her followers are customers who "pay for [Jason's] rent and his parenting money," and adding, "They are the people that are paying your legal bills." Bethenny then clarified that she asked her followers for guidance, if they had been in similar situations, which prompted Jason's attorney to ask, "Isn't a fact that you would rather take advice from 2 million followers [than] Jason?" That's when the judge intervened, telling Bethenny that she didn't have to answer that question, according to R Online. 

In Touch Weekly shared additional details about the social media discussion. Jason's lawyer asked Bethenny, "But if you were at the hospital already, what advice do you need?" At another point, Bethenny claimed that Bryn was sleeping and unaware that she had called on her followers for their input on how she should explain Cookie's passing to her young daughter.

In 2015, Bethenny Frankel opened up about her decision to marry Jason Hoppy at the NYU Alumni Association's Speakers on the Square event. "I think my instinct and gut going into my marriage [knew] it would turn out the way it did," she confessed (via People). "I could feel it, but I intellectualized it." Bethenny went on to quip, "It's all Andy Cohen's fault, he will admit it." She added, "I wasn't making a decision out of truth, I was making a decision out of fear." 

While Bethenny didn't specifically say why Andy was supposedly at fault, it should be noted that he wasn't listed as a producer for her Bravo spin-off shows on IMDb. However, she reflected, "Looking back on that, I don't really believe in regret, and it was situation where they were giving me a show — a spin-off — and I was in a relationship and it kind of just became, 'This is what's going on in your life, and this is compelling.'" Bethenny admitted, "It was hard for me to compartmentalize."

For his part, Andy told The Daily Dish, "I think they were really in love ... I think some people question themselves a lot and they just seemed to love each other and I was like, 'Do it, do it!'" However, Andy promised, "I don't have that kind of pull over her. Trust me, no one can tell her what to do."

During their May 2019 custody trial, Jason Hoppy's lawyer cited some plotlines from The Real Housewives of New York City as he questioned Bethenny Frankel. The attorney suggested that Bethenny was dishonest about her knowledge of Dennis Shields' possible overdose based on comments she made to a grief counselor during an episode that aired a month prior (via Page Six). Bethenny replied, "[It's] a show you shoot for seven days to get 40 minutes. I can never specifically say that's what happened. Even if you have a transcript, it might not be what I said." 

The judge interjected, "I do think it is bizarre [to ask about the show] ... We are taking this reality television show that was meant for entertainment value and supplanting testimony." Jason's lawyer suggested a "viewing party," which never happened. But unfortunately, these RHONY-related questions didn't end there. Bethenny was asked if she considered it "harassment" when her best-friend-turned-enemy, Carole Radziwill, described her as "a master of public promotion" and someone who is "quick to insult." Bethenny replied, "I don't think that's harassment, no. That's a comment, that's not calling me a name."

That's when the lawyer mentioned a Watch What Happens Live interview in which Bethenny called Carole a "b**ch" and "a f**king moron." Eventually, the judge stepped in, advising Jason's lawyer to ask questions about "the relationship between Mr. Hoppy and Ms. Frankel" instead of bringing up Bethenny's TV appearances.

Bethenny Frankel was very open when she was a cast member on The Real Housewives of New York City, especially during the early seasons. She even took a pregnancy on camera, with the bathroom door slightly open, during an episode that aired in April 2010. Bethenny's dog, Cookie, was by her side (along with the crew), but her then-boyfriend, Jason Hoppy, wasn't present. After completing the test, Bethenny tried to get in touch with Jason, calling him multiple times and sending messages.

Bethenny was stunned by the pregnancy, predicting, "I'll be happy in a few minutes," before admitting, "I'm a little freaked out." During the next episode, Bethenny was upset when the baby news leaked to the press. Consequently, she decided to confirm the pregnancy via Twitter in October 2009: "I'm pregnant. I had to be true w u but was unfairly forced to come forward early." 

In more recent years, Bethenny and Jason have been at odds over her public life, particularly when their daughter, Bryn, is involved. However, as Bethenny testified in March 2019 (via the Daily Mail), "We were in the hustle together. The publicity was part of our life for sure, and it was exciting." At this point, we imagine neither of them would use the word "exciting" to describe their ongoing legal struggles — but all publicity is good publicity, right? Well, maybe not in the case of Bethenny Frankel and Jason Hoppy.