Harry Dubin – Who is He Dating After His Relationships with Numerous Real Housewives?

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Harry Dubin is a wealthy businessman famous in the media as the womanizer from the Real Housewives Of New York City world. He has written a romantic saga with half of The Real Housewives Of New York City casts.

In fact, Dubin has become his storyline in the series. Over the years, he has turned into a magical mystique on the RHONY. In the past 13 seasons of the long-running Bravo series, he has topped the list among the men who have the most appearances on the show.

Additionally, no other man has hooked up with so many Housewives. He is often in the spotlight. Dubin has been around the RHONY for a significant time, but there are still new things about him. People close to Harry refer to him as charming, a good conversationalist, and a man with great wit.

So why is there so much attention? Know the reasons in the article below along with the fullest details of his dating history. Additionally unravel his origin story, his parental history, and more.

Harry Dubin Comes From A Wealthy Family

While Harry has lived and worked most of his life in the upper state, he originally is a southern guy. He has spent a lot of time in Washington D.C.

Page Six reports that Harry comes from a wealthy family. His family had been in the real estate business for ages. They operated mainly from Washington D.C.

Harry Dubin is the son of Richard Dubin and Elizabeth Dubin.
Harry Dubin is the son of wealthy parents operating from Washington DC.

Dubin’s mother Elizabeth’s family was the head of a well-established real estate business when she married his father, Richard Dubin. His father, whose nickname was “Dickie,” previously worked as a door-to-door Bible salesman in Boston.

Together, Richard and Elizabeth founded the Dubin Development in Bethesda, Maryland, which built thousands of residential and commercial units in the D.C./Maryland/Virginia area.

While Dubin’s father, Richard was a proud liberal, his mother, Elizabeth was a Republican. Dubin’s parents were together for 54 years before his father passed away on Christmas Day in 2015.

What Does Harry Do For A Living?

As for his job, Dubin doesn’t appear to have one. His ex-partner, Sonja once revealed that he lives off some kind of family trust that he uses to go out and look for a good time.

He, in fact, has got a big, fat trust fund. One of the leading ladies of RHONY added Dubin is among the people who have “Too much time, and too much money.”

However, by and large, he’s been reported to be a real estate investor and he’s been in it since a young age.

His Educational Background

Harry went to Walt Whitman High School and then attended college at Syracuse University before starting a successful real estate business in Manhattan.

He has a brother Louis Dubin who also works in real estate. Dubin also has a sister, Robin Avram.

Dubin resides in East Hampton, New York.

Harry Dated A Handful Of Celebrities – His Famous Romance With Sonja Morgan

The woman Harry dated included Morgan, de Lesseps, Singer, Bensimon, and Drescher.

His first ever known date was Sonja Morgan during the late ’80s to early ’90s. Harry’s relationship with Morgan was pretty serious.

They met when they were in their 20s and the time was before the days of cell phones.

Harry Dubin and Sonja Morgan dated each other during the late '80s and the early '90s.
Harry Dubin with his ex-girlfriend, Sonja Morgan

The real estate investor says he approached her while she was dancing, but only got her first name. Morgan was then staying at the Park Hyatt Hotel in Washington DC.

Eventually, they started seeing each other. They in the beginning had a long-distance relationship. Morgan resided in New York City, while Dubin was living in Washington D.C.

After some time, however, they split. Sonja Morgan states Dubin cheated on her when he was in D.C. and she was in New York.

Morgan and Harry, nonetheless, briefly got back together in Season 6 of RHONY. This time, Dubin even gave Morgan an “engagement ring.”

Though later there were reports stating it was all for the show. Morgan, however, refutes the rumor.

After a while, Harry yet again ended up ditching Sonja after giving her a promise ring to hang out with another girlfriend, Luann de Lesseps. Apparently, one of the reasons for the breakup was that Dubin tried to go for Luann de Lesseps.

What Did He Say About His And Luanna de Lesseps’ Relationship?

As for his connection with Luann, Harry says that they met at one of Sonja’s cocktail parties at her townhouse, about a year before she became a cast member.

Instead of going to dinner with the rest of the guests, Harry remembered de Lesseps suggesting she and Dubin go out on their own. Dubin said they had a very nice evening.

Harry Dubin allegedly ended his relationship with Sonja for Luann.
Harry Dubin with Luann de Lesseps.

The Washington DC native added,

“That’s the way Luann is. She goes after what she wants and she gets it. You can’t really deny that.”

Though the romance with Luann didn’t last either.

Aviva Drescher

Dubin then went on to have quite a solid bond with another RHONY cast, Aviva Drescher. Aviva appeared on the Bravo series in Seasons 5 and 6 and swiftly began dating Sonja’s former partner.

She would become the first among his other girlfriends whom he married. Though the date of their wedding to this remains a mystery.

With his ex-wife, Aviva Drescher, Harry has a son, Harrison.
From Left, Harry, his son, Harrison, and his ex-wife, Aviva Drescher.

They, however, would part ways in 2005. With Drescher, he has a son, named, Harrison.

Seven years after their separation, in 2012, Aviva alleged her former partner, Dubin failed to pay over $340,000 in child support.

Harry conversely denied his ex, Aviva’s allegations. It though remained unclear whether the pair settled the issue privately or in court.

As for Aviva, she is now in a marital tie with Reid Drescher.

Ramona Singer

In December 2018, Harry again made headlines when the media caught him kissing another RHONY star, Ramona Singer at a Manhattan restaurant.

Harry was also rumored to have date Ramona Singer.
In Dec 2018, some images aired over the internet which showed Harry kissing RHONY cast, Ramona Singer, on the left

The then newly-minted couple packed on PDA at Pomona restaurant in Midtown. Ramona Singer had also posted some pictures of her hanging out with Dubin. She though has since deleted the imaging.

People, however, believe it was a one-time ride anyway.

Kelly Bensimon

Another RHONY cast also is on the list of people that Dubin dated and she was a former model and a real estate agent, Kelly Bensimon. In Harry’s ex-wife, Aviva’s words, Dubin and Kelly dated off the camera.

Kelly Bensimon, an real estate agent, author, the editors and a former model.
Sonja Morgan’s ex-partner, Harry Rubin allegedly was also in a relationship with Kelly Robinson

Some insiders reported Harry vacationing with Kelly Bensimon in Miami. Kelly had starred on RHONY from Seasons 2 to 4.

Harry, however, denied the relationship was anything other than platonic.

In 2017, Harry also dated a woman named, Pamela Mitchell.

Who Is Harry Dubin Dating Now? 

As for the present, rumors have it Dubin is looking for a relationship with former Tiger Woods’ mistress, Rachel Uchitel.

In Jan 2021, the tabloids caught Dubin and Rachel Uchitel together in Palm Beach. They were at the public’s glance multiple times in the summer of 2021.

Rachel Uchitel is the ex-girlfriend of Tiger Woods.
As of late, Harry Rubin is reportedly dating Rachel Uchitel

Uchitel was with her daughter and Harry was also with his son, Harrison at Rocco’s Tacos.

Rachel, the ex-wife of Matt Hahn said,

“Harry and I have been super close friends for years. He is like family to me.”

Dubin, on the other hand, hinted at the possibility of a future relationship, telling Pag Six in the summer of 2021, “I do like her very much. We are great friends. Who knows where the future is gonna go?”

Harry Dubin’s Net Worth

Harry reportedly has a net worth north of $15 million. And given he was born with a silver spoon, that shouldn’t be surprising. As mentioned, he also has had success in real estate. And Sonja has also affirmed he was a privileged child.

The more than often luxury getaways, fancy dinners, and an undisclosed array of properties in New York, and in several other states should be enough for getting some perspective on the extent of his richness.


Narayan Shankar, who goes by the name David, is a seasoned writer and editor, who has a passion for covering the entertainment industry. He has years of experience writing content, especially in the entertainment niche. He is currently an editor and writer for celebsuburb.com along with other websites under our organization named Pandora Group of Companies.