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December 04, 2018 11:49 AM

He’s dated Luann de Lesseps, was nearly engaged to Sonja Morgan, and was once married to Aviva Drescher. And now, it appears, Harry Dubin has hooked up with another Real Housewives of New York City star.

The real estate investor, who has been a fixture on the Bravo reality series for years, was spotted on Friday in  Midtown N.Y.C. making out with O.G. Housewife Ramona Singer.

According to photos of their romantic rendezvous published by TMZ, Singer and Dubin got cozy at a private table at Pomona restaurant.

Tinsley Mortimer was also out with Singer that night, TMZ reports. As she’s said on the show before, Mortimer’s been a friend of Dubin’s for years; they met him long ago in Miami when he used to hang out with another ex-RHONY star, Kelly Bensimon. (Dubin’s also flirted with Alex McCord).

Ramona Singer and Harry Dubin
MARC DIMOV/Patrick McMullan/Getty

Singer, 62, and Dubin — who shares a son, Harrison, with Drescher — have also been friends for years, though it appears they never got romantic until now.

Back in June 2017, Singer said that she and Dubin were just pals and that she would never date him during a Watch What Happens Live with Andy Cohen after-show.

Still, she did explain Dubin’s appeal among the Manhattan singles: “He’s extremely charming and personable and fun to be with. And he’s kind-hearted and warm and generous.”

RELATED: Would Ramona Singer Ever Want to Get Married Again?

Singer has been single ever since her more than 20-year marriage to ex-husband Mario ended in 2014 amid his cheating scandal. Their divorce was finalized the following year.

Since then, Singer has remained active in the dating pool, telling PEOPLE in 2017 that “no one has stuck yet” but she’s “dating up a storm” and “dating men all over the country.”

So what exactly is Singer looking for in a guy? For one, she’d prefer he’s been married before (“it shows he’s willing to make a commitment”) — and someone who isn’t afraid of to jump at life’s many adventures. “

“I’m very social so I need someone who’s really social.” she said with a laugh “This one gentleman that I’m dating, I said, ‘Okay you ready for the Hamptons? We have like 10 parties to go to, and these are all parties at my friends’ private homes and each party is anywhere from 70-200 people.’ And he was like, ‘Let’s go!’ “

A man with children is also major plus since Singer has a close relationship with her 23-year-old daughter Avery.

“She so important to me in my life that if I was with a man who never had children, he could be jealous or resentful of the relationship that I have with my daughter,” Singer said. “I want him to have healthy relationship with his children, because family and friends are the most important thing. And children that are older — because at this point in my life my schedule is pretty free and if I want to hop on a plane one weekend to go to Aspen or California or Europe, I don’t want to hear, like, ‘Oh I have two children at home. It’s my weekend again. I have the kids!’ “

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