One of the most unforgettable and referenced episodes of The Real Housewives of New York is famously known as “Scary Island.” The episode, titled “Sun, Sand and Psychosis,” was part of Season 3. Ramona Singer hosted a girls’ trip to St. John island as a bachelorette celebration before her 17th anniversary vow renewal with her now ex-husband Mario Singer, inviting Bethenny Frankel, Alex McCord, Sonja Morgan, and Kelly Bensimon.

Kelly was already on shaky ground with Bethenny at the beginning of the trip. As the weekend progressed, Kelly’s behavior became increasingly erratic, leading to a confrontation at a dinner Bethenny had cooked for the group as a vow renewal present for Ramona. Kelly was triggered by a gift bag Bethenny left in front of each of their doors, which she deemed “impersonal.” She started crying and told the cameras she was “alone on Scary Island with no friends.”

During breakfast, Kelly got offended when Bethenny made a joke about stomping grapes to make wine for Ramona. Kelly was upset because she planned to eat the grapes. When Bethenny explained that she was using light humor and referencing the fact that wine was made by stomping grapes, Kelly maintained that she didn’t approve of “light humor” concerning food.

Things seemed to be going better later that night when the group had a nice dinner on the yacht. However, Kelly started unraveling again when the girls started talking about one-night stands, which Kelly found offensive. She then got confrontational with Sonja because she was crying about feeling insecure with her body after having a child. Sonja called Kelly out for not being okay when others were displaying strong emotions, and Kelly agreed and started mocking having feelings.

Kelly’s major gripe with Bethenny during the trip was over the fact that she thought Bethenny was defaming her in the press, an accusation she continued to make throughout their bizarre trip and later at the reunion. She never supplied evidence of what was said or that Bethenny was behind any press about Kelly or her family. Bethenny denied talking to the press about Kelly and her family.

Another huge gripe Kelly had with Bethenny was over Bethenny calling herself a “chef.” “You’re not a chef, you’re a cook. It’s creepy,” Kelly said to Bethenny. “I went to culinary school, you moron,” Bethenny responded.

The next night was when things really exploded. Kelly insisted on not sitting near or across from Bethenny, and when Bethenny served crab cakes, Kelly did not enjoy them. Later, she was given a raw steak with a string in it, which Bethenny immediately took back and redid. As the chaos escalated, Kelly claimed that Bethenny was trying to kill her.

She also accused Alex of wearing kabuki makeup and channeling a vampire when she confronted Jill.

What was going on with Kelly Bensimon on Scary Island?

In the 14 years since “Scary Island” aired, there’s been a lot of speculation about what happened. “I’m not a doctor, but something’s wrong. I’m worried for Kelly. Something’s going on here that is beyond just us,” Sonja says in an interview.

In 2021, Kelly published an explanation video about Scary Island titled “CLOSURE. Truth about Scary Island.”

In her video, Kelly said that she felt like the “new girl” and an outsider in the group.

There was a lot more to Scary Island

At the 2022 Bravocon, RHONY producer Matt Anderson shared that there was “a lot they didn’t show.” Kelly had actually been the first Real Housewife to break the fourth wall by calling out his name.

At the Season 3 reunion, Kelly said she had been a victim of “systematic bullying” from the rest of the girls and vowed to use her platform to educate young girls about systematic bullying.

Another odd aspect of Scary Island was Kelly’s preoccupation with gummy bears and jelly beans. When everything unraveled at the end, Kelly went and got her jelly beans and started munching on them and offering them to everyone while Bethenny yelled at her to “GO TO SLEEP.”

Later, when Kelly unsuccessfully tried to explain to Luann and Jill what happened, they laughed at her when she mentioned bringing out the jellybeans.

This trip was iconic for several reasons. The night before Kelly’s major breakdown, Ramona debuted “Turtle Time.”

During another chaotic situation with Kelly, a very drunk Ramona had hopped over from the girls’ yacht to the nearby yacht of the owner of Hooters, who heavily flirted with her. When she was done with the Hooters yacht, Ramona convinced Bethenny and Alex to join her at the Fat Turtle bar to dance for a while.

Ramona said that it was the “best night I’ve ever had with girlfriends” she said in confessional.