The infamous “Scary Island” trip from The Real Housewives of New York City continues to captivate fans, and now, 15 years later, cast member Kelly Bensimon is finally pulling back the curtain on the chaotic vacation that cemented its legendary status in reality television history. Her exclusive insights reveal the true extent of the drama that unfolded during the 2010 St. John getaway, a trip widely regarded as one of the wildest in the franchise’s extensive run.
Far from a relaxing escape, Bensimon recently shared her personal disillusionment with the experience. During a recent iHeartRadio and Pickleball Tournament event in Lake Tahoe, she candidly expressed her frustration, noting, “I didn’t get to do anything fun. I didn’t get to get drunk. I didn’t get to roll around in the leaves or the bushes. I didn’t get to meet the pirate. I didn’t get to have any fun. All I got to do was, like, eat jelly beans and get yelled at. Like, that is not fair.” Her remarks underscore the intense and often isolating nature of her time on Scary Island.
The Real Housewives of New York City, which first aired in 2008, quickly became a cultural phenomenon, introducing viewers to a dynamic ensemble of affluent New York women. While the inaugural season featured familiar faces such as Luann de Lesseps, Ramona Singer, Bethenny Frankel, Jill Zarin, and Alex McCord, Kelly Killoren Bensimon joined the cast in season two, adding a new layer of personality and conflict to the show’s evolving narrative. Sonja Morgan later became a full-time cast member, further shaping the show’s iconic lineup.
The cameras famously captured Kelly’s struggles to integrate and find common ground with fellow housewives Bethenny Frankel and Ramona Singer. The tensions peaked dramatically, leading to one of the most memorable moments in reality TV history when a cast member famously commanded Kelly to “Go to sleep!” This explosive confrontation became a defining moment of the trip, highlighting the deeply fractured dynamics within the group and cementing Scary Island’s place in Bravo lore.
The intense environment prompted Bensimon to consider an early exit from the show. She recounted calling her agent directly from the boat, stating, “This is where we’re done here. This is not going my way. There are things that are happening that are organized and I am going to be this villain for no reason.” Despite her profound discomfort and feeling unfairly targeted, Kelly ultimately remained with the series through the end of season four, enduring the pressures of reality television.
Before her departure, Kelly Bensimon, who now hosts iHeartRadio’s “I Do, Part 2,” participated in another notable cast trip to Morocco, offering a different, albeit still dramatic, experience. Despite the intense negativity she faced during the St. John vacation, Bensimon revealed her commitment to professional courtesy, always sending a thank-you card to her cast members and the crew upon returning home to New York.
As a Douglas Elliman real estate agent, Bensimon emphasized her dedication to her role on the show. “I always send a thank you note,” she explained. “It’s important because it’s our job. We’re working, and I just want to say thank you. I appreciate what we do together, and the fans may see it a different way, but for me, I work really hard and I take it really seriously, and I make a concerted effort to be present. I really loved my time on Housewives.” Her reflection offers a nuanced perspective on the demanding nature of reality TV and her personal commitment to the work.
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