Kelly Bensimon doesn’t hesitate to walk away when something feels off, especially in her love life. The Real Housewives of New York alum and current real estate agent recently paused her budding relationship with Connecticut-based financier Robert Flood after an unexpected downpour of drama came crashing in. Just as everything seemed to be smooth sailing, then came a tsunami of receipts.
While Kelly was prepping to walk in Miami Swim Week, her DMs blew up. Right before she hit the runway, she received a message she couldn’t ignore.
Kelly Bensimon was flooded with DMs about Robert Flood

Kelly explained to Us Weekly that someone slid into her DMs with some disappointing tea about Robert. Kelly recalled, “I was in hair and makeup and my DMs started going off.” “A woman I know said, ‘I saw your boyfriend in my hometown making out with some woman.’”
She tried to keep it cool. “It was early days and I’m glad he’s having fun.” But her friend didn’t let it slide so easily, and neither did the receipts.
The messages didn’t stop, even after Robert joined her in Miami. Kelly got on the phone with her friend, who revealed the woman was his ex-fiancée, and the make-out allegedly lasted 90 minutes.
Kelly admitted, “I was just sad, genuinely sad for all of us.” “It’s hard for me to trust and to feel safe. So, I put Robert in short-term parking.”
Kelly didn’t hold back while confronting the “kissing bandit.” “I told him, ‘You date people, I’ll date people and if it’s the right thing to do, we’ll figure it out.’”
The couple first connected on Hinge, but Kelly’s now having second thoughts. “Are these dating apps what they say they are?”
She laughed, “I cannot date a guy that has better photos than me,” she explained. “And I cannot date a guy that wears smaller jeans than I do. Those are two of my rules.”
Kelly’s fellow Housewives supported her. “I was texting with Jill Zarin yesterday. She’s like, ‘How’s dating?’ and I’m like, ‘I date guys that cheat on me … guys that aren’t interested in me … And then I date guys that have also gone out with Bethenny Frankel. It just doesn’t end.’”
The Countess weighed in too. “Luann [de Lesseps] tells me, ‘Darling, why don’t you have a little more fun?’ She was like, ‘I can’t believe you did not come to Love Hotel.’”
After calling off her wedding with ex-fiancé Scott Litner just four days out, and now this, Kelly’s wondering if she’s doomed. “What is wrong with me? Do I have the Housewives curse?”
However, Kelly’s keeping the door open for both love and TV. “I would definitely go on a show like that, a hundred percent,” she said about Golden Bachelorette.
“I always have been open for love,” she added. “But whoever it is, they have to show up. I’m in my, ‘You-Have-to-Show-Up era.’”