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Home Entertainment

Kelly Bensimon ‘Pumps the Brakes’ on Relationship With Robert Flood

by DigestWire member
June 27, 2025
in Entertainment
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Kelly Bensimon ‘Pumps the Brakes’ on Relationship With Robert Flood
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Kelly Bensimon hit pause on her relationship with Robert Flood — and the story sounds like something out of a Housewives episode.

The former Real Housewives of New York City star, 57, was getting ready to open Swim Week in Miami for Melissa Odabash’s show when she got an unexpected message about the Greenwich-based financier.

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

At first, the real estate mogul tried to brush it off, replying, “It was early days and I’m glad he’s having fun.” But her friend encouraged her to take the situation more seriously.

Kelly Bensimon
Sergi Alexander/Getty Images

Even after Flood joined her in Miami, the messages kept coming. Eventually, Bensimon hopped on a call with her friend, who confirmed the woman in question was his ex-fiancé and that the make out session reportedly lasted 90 minutes.

“I was just sad, genuinely sad for all of us,” she shared. “It’s hard for me to trust and to feel safe. So, I put Robert in short-term parking.”

She did eventually confront Flood, calling him a “kissing bandit.”

Kelly Bensimon Shades Bethenny Frankel and ‘Housewives Fanatic’ Boyfriend

“I told him, ‘You date people, I’ll date people and if it’s the right thing to do, we’ll figure it out.”

Bensimon and Flood originally met on Hinge, a platform that Bensimon is now rethinking.

She asked: “Is Hinge looking for love in all the wrong places? Are these dating apps what they say they are?”

Bensimon describes her current relationship with dating apps as “on a pause.”

She says that Raya is “not for me,” but it’s helped her realize she has two important non-negotiables when it comes to finding a relationship.

“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.”

She laughed, adding, “Like, ‘Do they have a job?’ I’m like, “No, but they don’t wear jeans that are smaller than mine.”

‘RHONY’ Alum Kelly Bensimon Puts ‘Family First’ on Would-Be Wedding Date

Recently on the I Do, Part 2 podcast, Shannon Beador chatted with Bensimon about her dating experiences post-Love Hotel. Shannon mentioned that her date “kissed me in public,” and noted that it was a red flag with Flood that he kissed Kelly in public. Both women are not fan of PDA.

When it comes to what she is looking for, Bensimon has some important criteria: “It’s not like you have to have a private plane, not the Housewives’ bulls***. It’s real life. Consistency. Kindness. Good man. Strong moral compass. Make me feel safe.”

As the drama unfolded, Bensimon leaned on her Housewives friends for support.

“I was texting with Jill Zarin yesterday,” she said. “She’s like, ‘How’s dating?’ and I’m like, ‘I date guys that cheat on me. I date guys that aren’t interested in me. I date guys that want to be in the press. And then I date guys that have also gone out with Bethenny Frankel. It just doesn’t end.’”

“Luann [de Lesseps] tells me, ‘Darling, why don’t you have a little more fun?’ She tells me to date everybody. She was like, ‘I can’t believe you did not come to Love Hotel.’”

After a broken engagement last year with ex-fiancé Scott Litner, and this situation with Flood, Bensimon is wondering, “What is wrong with me? Do I have the Housewives curse? How come I’m always the scapegoat? How come I don’t deserve love? How come I’m always the scapegoat? I was a scapegoat on Housewives. I am the scapegoat in my personal life.”

Why Kelly Bensimon Was ‘Not Prepared’ for Her Surprise Engagement

Still, Bensimon remains open to love — and reality TV.

She would “definitely” appear on Golden Bachelorette or Love Hotel.

“I would definitely go on a show like that, a hundred percent. I mean, who knows if one of the guys from the Golden Bachelor were a smoke show?” she said. “I think I might be a little young, but I love that. Joan had a really good experience, she had so much fun and met some really nice guys.”

She added, “I always have been open for love. I feel that love is in the air and who knows what’s going to happen. But whoever it is, they have to show up. I’m in my, ‘You-Have-to-Show-Up era.”

Us Weekly has reached out to Flood for comment.

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