Luann de Lesseps’ Ups and Downs: A Timeline of the ‘Real Housewives of New York City’ Star’s Struggles

Credit: Patrick McMullan via Getty Images

Luann de Lesseps’ Ups and Downs: A Timeline of the ‘Real Housewives of New York City’ Star’s Struggles

As Luann de Lesseps once declared, “The most interesting people make the best headlines.” While the Real Housewives of New York City star has been a part of the franchise since its 2008 premiere, her offscreen drama didn’t start turning heads until her relationship with Tom D’Agostino Jr. Luann was previously married to Count Alexandre de Lesseps. The twosome, who share daughter Victoria and son Noel, called it quits in 2009 after 17 years of marriage. Following a relationship with Jacques Azoulay, the “Money Can’t Buy You Class” singer met Tom. Despite the businessman’s messy past with her costars Sonja Morgan and Ramona Singer, Luann fell quickly for Tom. After a whirlwind romance, the duo announced their engagement in February 2016. "Thomas wanted to do the honor on Valentine's Day, but just couldn't wait and gave Luann an 8-carat canary yellow diamond ring,” Luann’s rep said in a statement to Us Weekly at the time. “Luann is 'over the moon' in love with Thomas, considers him her soul mate and is so happy and grateful to have found love a second time.” As the pair planned their wedding during season 8 of RHONY, Bethenny Frankel discovered that Tom had been unfaithful. Still, Luann went threw with the wedding. Less than a year after their 2016 New Year’s Eve nuptials, however, Luann and Tom called it quits. In December 2017, Luann returned to Palm Beach — where she wed Tom nearly a year earlier — and was arrested and charged with battery, trespassing and disorderly intoxication. After she was released, Luann rang in the new year in rehab. Since then, the reality star’s journey to maintain her sobriety — and avoid jail time — has continued to make headlines. Scroll through for a complete timeline:

Credit: Patrick McMullan via Getty Images

Luann de Lesseps’ Ups and Downs: A Timeline of the ‘Real Housewives of New York City’ Star’s Struggles

As Luann de Lesseps once declared, “The most interesting people make the best headlines.” While the Real Housewives of New York City star has been a part of the franchise since its 2008 premiere, her offscreen drama didn’t start turning heads until her relationship with Tom D’Agostino Jr. Luann was previously married to Count Alexandre de Lesseps. The twosome, who share daughter Victoria and son Noel, called it quits in 2009 after 17 years of marriage. Following a relationship with Jacques Azoulay, the “Money Can’t Buy You Class” singer met Tom. Despite the businessman’s messy past with her costars Sonja Morgan and Ramona Singer, Luann fell quickly for Tom. After a whirlwind romance, the duo announced their engagement in February 2016. "Thomas wanted to do the honor on Valentine's Day, but just couldn't wait and gave Luann an 8-carat canary yellow diamond ring,” Luann’s rep said in a statement to Us Weekly at the time. “Luann is 'over the moon' in love with Thomas, considers him her soul mate and is so happy and grateful to have found love a second time.” As the pair planned their wedding during season 8 of RHONY, Bethenny Frankel discovered that Tom had been unfaithful. Still, Luann went threw with the wedding. Less than a year after their 2016 New Year’s Eve nuptials, however, Luann and Tom called it quits. In December 2017, Luann returned to Palm Beach — where she wed Tom nearly a year earlier — and was arrested and charged with battery, trespassing and disorderly intoxication. After she was released, Luann rang in the new year in rehab. Since then, the reality star’s journey to maintain her sobriety — and avoid jail time — has continued to make headlines. Scroll through for a complete timeline:

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August 2017 — It’s About Tom

Luann gave an emotional interview to Andy Cohen following her split. “Tom went out and he called up an old girlfriend and they met up with a group of people and I didn’t know about it,” she explained at the time. “I found out about it the next day in the press, so that for me was, like, the final straw. I was like, ‘I can’t do this anymore.'”

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December 2017 — Arrest

According to a police report obtained by Us, Luann trespassed in a hotel room with an unidentified man shortly before she was booked in Palm Beach on Christmas Eve 2017. The reality star was then accused of assaulting a police officer as he attempted to take her into custody. “[Luann] slammed the door on Officer O’Leary’s face, striking him in the forehead,” the police report read. After she managed to slip out of her handcuffs, Luann told the officer she was “going to f–king kill all of you,” per the paperwork.

Luann was charged with battery, trespassing and disorderly intoxication. At the time, she blamed her behavior on her split from Tom.

“I want to offer my most sincere apologies to anyone that I might have offended with my behavior,” she tweeted. “This was my first time in Palm Beach since my wedding and being here brought up buried emotions. I am committed to a transformative and hopeful 2018.” 

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January 2018 — Rehab Round One

Following her arrest, Luann checked into treatment. She completed her first stint before the end of January 2018. “It’s good to be home. I’m doing great,” she tweeted on January 23, 2018. “Spending time with friends and family. Thanking  everyone for your continued good wishes and support.” 

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April 2018 — Moving On

Luann told Us in April in 2018 that she had “gotten past” her dark period. “I’m not totally through it completely, but I’m optimistic it’s going to turn out well and everything is going in that direction for me, so I feel very positive,” she said at the time. 

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July 2018 — Lawsuit

The “Girl Code” songstress hit a rough patch when her ex-husband and two kids filed a lawsuit against her, citing a breach in the former couple’s divorce deal. According to the court documents obtained by Us in July 2018, Alex, Victoria and Noel claimed Luann purchased a $3.1 Sag Harbor, New York, estate in 2013 without creating a trust that would entitle the kids to the home as outlined in the divorce proceedings. She was also accused of threatening to sell the home and buy a new house in upstate New York without providing the children with their entitled share of the funds. (The lawsuit was dropped in April 2019.)

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July 2018 — Rehab Round Two

Days after news of the lawsuit broke, Luann checked back into rehab following an intervention led by her costar Bethenny Frankel. As a result, Luann missed the season 10 reunion taping. “Bravo supports Luann’s decision to focus on her health. She is part of the Bravo family and we continue to stand by her as she copes with this challenging situation,” the network told Us at the time. “At this time, we hope everyone will respect her privacy.”

Luann later admitted that being sued by her kids was “a big hiccup.” 

“[It was] about me wanting to get a house upstate and not being in the Hamptons, so I decided to keep the Hamptons home and I’m getting a house upstate in any case,” she said on Watch What Happens Live With Andy Cohen in September 2018. “So it all worked out.”

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August 2018 — Plea Deal

Luann avoided jail time for the first time in August 2018 by accepting a plea deal. In addition to one-year probation, Luann was ordered to complete 50 hours of community service, go to two Alcoholics Anonymous meetings per week and attend a victim impact class with Mothers Against Drunk Driving.

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March 2019 — Taking it Day by Day

The reality personalty told Us in March 2019 that she was taking her sobriety “day by day.”  

“I do the best that I can do. I get on the stage and that keeps me busy and it keeps me focused on my cabaret, and I get to put my creative energy into that and it keeps me out of trouble,” she said. “I’m just doing yoga and taking care of myself and hanging out with less people that are prone to partying.”

While her castmates worried that performing her Countess and Friends cabaret would affect her sobriety, Luann told Us that wasn’t the case.

“It’s not that I can’t be around people that party. Not at all. I mean, I’m around the cabaret industry,” she explained. “I filmed an entire season without drinking. If you can get through Housewives without drinking, you can get through anything.”

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April 2019 — Relapse

A month later, Luann failed an alcohol test. According to the paperwork previously obtained by Us, she admitted to having “2 glasses of mimosas after a performance she had in Chicago” in April 2019. At the time, Luann was "offered the opportunity to immediately enroll in outpatient treatment," but declined because of her cabaret touring schedule. She also opted not to wear an alcohol ankle monitoring device because it would be “too intrusive.”

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May 2019 — Back to Jail?

Following her relapse, Luann was ordered to appear in Palm Beach court. While a judge initially ordered the RHONY star back to jail, reportedly telling her she didn’t take her probation seriously enough, she ultimately struck a new plea deal and was released from custody.

“These reports are false. I’m glad the judge was understanding once made aware of the evidence provided and I was then released,” Luann said in a statement to Us on May 23, 2019. “I am now looking forward to completing my remaining few months of probation. I want to put this behind me and move forward with my life.”

The terms of Luann’s second plea deal were much stricter, according to court documents. In addition to “weekly telephone counseling sessions” and “monthly in-person sessions” with her treating psychiatrist, Luann was ordered to maintain a “breathalyzer monitoring device” as directed by her probation officer. She was also instructed to take Antabuse, an alcoholism medication, as prescribed by her doctor.

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August 2019 — Probation Over

Luann announced that she completed probation in a handwritten note shared via Instagram. “I’m happy to say after a long difficult year ….. I’ve made it through!” she wrote. “I’m humbled and grateful for this life lesson and ready to put the past behind me and move on with my life. Wish me luck! Thank you for your undying support over the years! Love always, Luann.”

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January 2020 — Drinking Again

Multiple sources confirmed to Us that the Bravo star was drinking again following her probation-mandated sobriety.