One of the most remembered and referenced episodes of Real Housewives of New York is known as “Scary Island” because that’s what Kelly Bensimon called it. The episode, which is number 12 of Season 3, is called “Sun, Sand and Psychosis.” It originally aired on May 20, 2010.
Ramona Singer hosted Bethenny Frankel, Alex McCord, Ramona Singer, Sonja Morgan, and Kelly Bensimon on a girls’ trip to St. John island as a sort of bachelorette celebration before her 17th anniversary vow renewal with her now ex-husband Mario Singer..
Kelly was already in a precarious spot with Bethenny at the beginning. As the trip wore on, Kelly revealed she was having nightmares because she was paranoid that Bethenny would kill her in her sleep. Kelly’s behavior continued to unravel over the weekend, leading to a confrontation at a dinner Bethenny had cooked for the group as a vow renewal present for Ramona.
Kelly was immensely triggered by a gift bag Bethenny left in front of each of their doors. “I don’t get why she did this. I don’t get why she did this,” Kelly said. “It was so impersonal, and it just rubbed me the wrong way.”
She started crying and told the cameras she was “alone on Scary Island with no friends.”
During a breakfast Kelly got offended because 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 was 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. The group had a nice dinner on the yacht, and then Bethenny started opening up about the recent death of her father.
Kelly started unraveling again when the girls started talking about one night stands, which Kelly found to be offensive.
She then got confrontational with Sonja because 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. “To be honest with you, the whole feelings thing? It’s like 1979.”
She then went after Bethenny, saying that she likes to play the victim and that she tries to make people feel bad so she can feel better.
One of Kelly’s major problems with Bethenny during the trip was over the fact that she thought Bethenny was defaming her in the press, an accusation she continued to makeup 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.
Things started off pretty calm, but Kelly insisted on not sitting near or across from Bethenny.
At first Bethenny was coming in and out because she was running the kitchen.
Kelly did not enjoy the crab cakes Bethenny served, and later was given a raw steak with a string in it that Bethenny immediately took back had redone.
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.
At one point, the rest of the girls left Sonja alone with Kelly, and Kelly confided in Sonja that she was still torn up about her belief that Bethenny disparaged her kids to the press.
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 interview.
“I think Kelly is incredibly paranoid, incredibly delusional. I really believe that Kelly believes her own myth, I do. Why would I spend my time to put Kelly in the paper?” Bethenny questioned.
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.
What did Bethenny Frankel do to Gwyneth Paltrow?
During one particularly memorable moment, Kelly asked Bethenny “Why about when you attacked Gwyneth, my friend Gwyneth?”
“Who’s Gwyneth,” Bethenny queried.
“Paltrow!” Kelly asked.
What Bethenny did to Kelly’s friend Gwyneth Paltrow was never addressed, but there is an interesting article from 2009 quoting Bethenny making a negative quip about watching Gwyneth Paltrow cook.
“I’d rather staple my eyelids shut than watch Gwyneth cook,” Bethenny said at the Montauk Yacht launch of her SkinnyGirl Margarita when asked about the potential of a Gwyneth Paltrow cooking show.
Gwyneth is afraid to [reveal] who she really is – she’s so manhandled by publicists and managers,” she continued. “Her show would be way too boring to watch.”
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.
“It was a crazy night. Kelly felt like she had to stay at that dinner … and we kept saying, ‘If you’re agitated, you can leave,’” Anderson said. “She didn’t like where it was going, so she just said my name over and over. She goes, ‘Matt, Matt, Matt, Matty, Matty’…and that’s where [it was like], ‘Go to sleep!’”
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 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.
