Kelly Bensimon’s Relationship With Robert Flood Uncertain After PDA With His Ex

Kelly Bensimon is rethinking her relationship with financier Robert Flood after he was spotted kissing his ex-fiancée. The former “Real Housewives of New York” star was getting ready to strut the runway in the Melissa Odabash show in Miami when DM’s started flooding in. 

“I was in hair and makeup and my DMs started going off,” Bensimon told Us Weekly. “A woman I know said, ‘I saw your boyfriend in my hometown making out with some woman.’”

At first, Bensimon, 57, didn’t think much of it, and Flood even came to join her in Miami. But the DMs didn’t stop. Bensimon’s friend broke it to her that the woman she’d seen was Flood’s former fiancée and their PDA was more than just a peck on the lips. 

Bensimon confronted her “kissing bandit” boyfriend, telling him they should both date other people for a while. “I was just sad, genuinely sad for all of us,” she explained. “It’s hard for me to trust and to feel safe. So, I put Robert in short-term parking.”

Bensimon Is Over Dating Apps

Bensimon was married to famed photographer Gilles Bensimon from 1997 until 2007 and they share two daughters, Sea and Thadeus. In June of 2024, the former model called off her engagement to Scott Litner just days before their nuptials. 

Later that year, Bensimon revealed she’d connected with a man on the dating app Raya who turned out to be dating her former “RHONY” cast member Bethenny Frankel. And it was on another dating app, Hinge, that Bensimon met Flood. 

But now Bensimon is questioning whether the apps are worth the trouble. “Is Hinge looking for love in all the wrong places?” she mused. “Are these dating apps what they say they are?” 

She told US Weekly that currently she is “on pause” when it comes to dating apps, but she has figured out what she’s looking for in a partner: “Consistency. Kindness. Good man. Strong moral compass. Make me feel safe.”

Bensimon Looks to Her ‘RHONY’ Pals for Advice

In the wake of the drama with Flood, Bensimon has turned to several of her “RHONY” friends for support. She said she’d been texting with Jill Zarin who asked about her dating life. “I’m like, ‘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.’”

Her buddy Luann de Lesseps shared some very Luann-esque advice. “[She] tells me, ‘Darling, why don’t you have a little more fun?’ She tells me to date everybody,” Bensimon revealed. 

But Bensimon couldn’t help but wonder if her “Real Housewives” past had something to do with her dating troubles. “Do I have the ‘Housewives’ curse?” she said. “I was a scapegoat on ‘Housewives.’ I am the scapegoat in my personal life.”