Kelly Bensimon, the poised and polished former star of The Real Housewives of New York, found herself at the center of a romantic whirlwind just as she was preparing to dazzle on the runway at the Melissa Odabash show in Miami. The 57-year-old reality TV icon was in the midst of hair and makeup when her phone buzzed incessantly with DMs that would soon upend her world. “A woman I know messaged me, saying, ‘I saw your boyfriend in my hometown making out with some woman,’” Bensimon shared with Us Weekly. At first, she brushed it off as a misunderstanding, but the truth proved harder to ignore.
The financier Robert Flood, Bensimon’s boyfriend, had been spotted in a compromising embrace—not just with any woman, but his former fiancée. The news hit Bensimon like a tidal wave, especially as the DMs kept pouring in, confirming the public display of affection was far more than a fleeting moment. Flood even joined her in Miami, but the damage was done. Heartbroken yet resolute, Bensimon confronted him, suggesting they both explore other options for the time being. “I was just sad, genuinely sad for all of us,” she admitted. “It’s hard for me to trust and to feel safe. So, I put Robert in short-term parking.”
A Rocky Road in Love
Bensimon’s romantic journey has been anything but smooth. Previously married to renowned photographer Gilles Bensimon from 1997 to 2007, she shares two daughters, Sea and Thadeus, with her ex-husband. More recently, in June 2024, she made headlines when she called off her engagement to Scott Litner mere days before their planned wedding. Now, her relationship with Flood—whom she met on the dating app Hinge—has hit a rough patch, leaving her questioning her approach to finding love.
Adding a twist to her tale, Bensimon revealed a curious coincidence from her time on another dating app, Raya. There, she connected with a man who, unbeknownst to her, was also dating her former RHONY co-star Bethenny Frankel. The overlap left her reeling, and now, with the Flood drama unfolding, she’s ready to hit pause on dating apps altogether. “Is Hinge looking for love in all the wrong places?” she mused to Us Weekly. “Are these dating apps what they say they are?”
For now, Bensimon is clear about what she wants in a partner: “Consistency. Kindness. A good man with a strong moral compass who makes me feel safe.” It’s a simple yet profound checklist, born from years of navigating high-profile relationships and their pitfalls.
Leaning on Her RHONY Sisters
In the wake of this latest romantic setback, Bensimon has turned to her Real Housewives confidantes for support. She’s been texting with Jill Zarin, who probed about her dating life, only to hear Bensimon’s wry response: “I date guys that cheat on me … And then I date guys that have also gone out with Bethenny Frankel. It just doesn’t end.” Meanwhile, the ever-glamorous Luann de Lesseps offered her signature flair, advising, “Darling, why don’t you have a little more fun? Date everybody!”
Yet, amidst the camaraderie and sage advice, Bensimon can’t shake a nagging thought: Is there a Housewives curse haunting her love life? “I was a scapegoat on Housewives,” she reflected. “And I am the scapegoat in my personal life.” Whether it’s a curse or just bad luck, Bensimon remains undeterred, determined to find a love that matches her strength and spirit.