25 most outrageous moments in Real Housewives history

Kelly turns their getaway into Scary Island- RHONY

After her short stint on the New York installment, Kelly Bensimon fought hard against her “crazy” persona. She did the press rounds and tried her best to do damage control, but there wasn’t much she could do after that first season’s showing, specifically the two episodes fan affectionately know now as “Scary Island.”

Way back in season three, when Housewives’ audiences weren’t used to the extreme personalities and overblown freakouts, we got Kelly Bensimon. Seemingly laid back and chill, she quickly became a polarizing force. When all the ladies went on a tropical vacation for Ramona’s bachelorette party for her vow renewal (RIP Ramona and Mario’s marriage), we watched as Kelly slowing unraveled.

Reacting to what she called “systematic bullying,” she just couldn’t get herself together. She was combative and argumentative and carried herself like she was simply above the drama — not a good look for a Housewife. Her main adversary was Bethenny Frankel, and you can imagine how well that went for her.

Kelly’s snarkiness and pettiness reached it’s most worrisome at a dinner with all the ladies. Disheveled and appearing confused, she tried to hold her own in the argument by insisting she didn’t care about any of them or anything related to them. After fits over jellybeans and semantics, it became clear to the rest of the group that she was struggling. At one point, after Kelly’s insistence that everything was “gross” and “stupid” Bethenny screamed, “THEN GO TO SLEEP.” Cementing this moment in the Housewives canon.