Former model Kelly Bensimon had an interesting summer dating experience. She joined the celebrity dating app Raya and started scrolling through profiles. She came across a cute guy from California who kept asking her to meet up, but her busy schedule got in the way. They were texting quite a bit until she found out he was dating Bethenny Frankel.

Surprise and Shock

After spending Labor Day weekend in the Hamptons separately, Bensimon's friend sent her a Page Six article revealing that Bethenny Frankel was dating the same guy. She was just as surprised as before, exclaiming, "Wait, what?! Again?!" This isn't the first time such a thing has happened to her.

Frankel's New Romance

Last month, Bethenny Frankel hard launched her relationship with California-based businessman Tom Villante on Instagram. On September 8, they were photographed smiling and holding hands on a date night in Los Angeles at Giorgio Baldi, a celebrity hotspot. Villante is the chairman and CEO of YapStone, a mobile platform that converts bills into online electronic payments. He sold his Malibu mansion for $35 million in 2020, double the price he paid. He is Frankel's first boyfriend since her March split from fiancé Paul Bernon.

Bensimon's Dating Life

For Bensimon, her dating life took a turn in August. She called off her wedding to financier Scott Litner in June, just four days before the ceremony. But she was casually dating again by that time. She had that initial connection on Raya and the subsequent drama with Bethenny Frankel's relationship. It shows the ups and downs of the dating world even for celebrities.