Kelly Bensimon had her eyes on The Golden Bachelorette runner-up Guy Gansert — until he revealed he was off the market.
The Real Housewives of New York City alum, 56, explained on the Wednesday, March 19, episode of iHeart Radio’s “I Do Part 2” that she previously played a dating game on the podcast, where she met Guy, 66, and fellow The Golden Bachelorette contestant Gary Levingston.
“One of the guys that I picked, he’s a doctor,” she said. “He seemed very organized with his thoughts and his intentions and I was like, ‘You know what, that’s what I need.’ I’m looking for solid. I’m looking for the rock. I’m not looking for the roll.”
Kelly claimed Guy asked for her phone number and proceeded to text her “novellas,” explaining that the messages were “so long.”
“So I text back and I’m like, ‘That’s great.’ That’s how I text back. I’m like, ‘That’s great, sounds fun, look forward to, can’t wait, whatever,’” Kelly said. “And it was like … ‘I like this and I like that, and I think you’d like this, and I think you’d like that,’ and going on and on and on and on and ‘Here’s a photo of me without a pocket square.’ I was like, ‘What is going on?’”
Kelly alleged that things changed in her texting relationship with Guy.
“Because he knew we were coming here, he was like, ‘Oh, by the way, I’m dating someone. Here’s her name.’ And I was like, ‘Wait, I’m sorry, what?’” Kelly said, claiming that Guy continued to send her “more images” of himself and told her he’s an “actor.” (Guy guest starred on an episode of General Hospital earlier this month.)
While things didn’t work out between Kelly and Guy, she went on to pursue a connection with Gary, 65 — going on their first date at the 2025 iHeart Radio Music Awards.
“It’s the best date I’ve ever had,” Kelly gushed to Us Weekly at the Monday, March 17, event in Los Angeles.
As she recapped her date night with Gary, Kelly reflected on how far she’s come since she called off her wedding to Scott Litner days before the pair exchanged vows.
“If this had been a year ago, I would’ve been like, ‘No, I can’t do that.’ But I’m in such a good place. It’s interesting because I said, ‘I really appreciate being with you. We’re having so much fun,’” she said. “Because Guy had said he couldn’t walk the carpet because he had fallen in love and he was going on a TV show. I was like, ‘That’s great.’ Then he kept texting me saying, ‘Is it real?’ And I was like, ‘I don’t know what you’re talking about. We haven’t even met yet.’”
Gary, for his part, gushed that Kelly “exceeded” his standards for fun. “Just being her and who she is, just her personality and her character, made it easy for me,” he said. “So it was fun. Absolutely.”
