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Harry Dubin Made Surprise Appearance on RHUGT — and One Hookup Rumor Was Finally Put to Bed
The New York businessman — once romantically linked to several of the RHONY cast members — surprised them on their trip to St. Barts.
If ever there was an ultimate Househusband that never was, it might have been Harry Dubin, who just made an epic appearance on The Real Housewives Ultimate Girls Trip.
Fans of The Real Housewives of New York City might fondly (or not-so-fondly) recall wealthy real estate investor Harry Dubin making his rounds through New York’s high society. With marriages, romantic relationships, and alleged hookups with a handful of the Housewives over the years, his reputation as the ultimate RHONY playboy lives on.
And in case you need a refresher course after his RHUGT appearance, we’ve got you covered.
Why Harry Dubin appeared on RHUGT
If fans found themselves jumping from their seats at the mere mention of Harry on RHUGT Season 4, they weren’t alone. In Episode 5, it was Dorinda Medley, Luann de Lesseps, and Ramona Singer (Team One) versus Kelly Killoren Bensimon, Kristen Taekman, and Sonja Morgan (Team Two) on a laugh-out-loud scavenger hunt on their St. Barts vacay.
For their last hint, Team Two read from a card: “If you’re seeking answers, feeling askew, one name stands tall with the wisdom anew. Dial Harry Dubin, he holds your final clue.”
RELATED: Dorinda Medley Has an Unexpected Love Life Update: Exclusive
The women had a lot to say before making the call, including his ex-girlfriend Sonja, who called Harry her “nemesis.”
“Why is Harry always involved?” asked Ramona.
“We can’t get away from Harry,” Dorinda told RHUGT producers. “Before we know it, you guys will be driving us to The Regency.”
Dorinda’s comment was a nod to the New York City hotel bar, one of Harry’s notable haunts.
Harry, on the phone for the scavenger hunt, said it was “the first time in Housewives history” that all the women were quiet, to which Sonja responded, “Read the f-cking clue, Harry.”
All players had to fill in the blank when Harry stated, “Fierce and bold, their stories unfold, legends untold. What they leave behind for all to see, a single word, their lasting ______.”
Kristen correctly guessed “Legacy,” leading Team Two to victory and snagging gift cards to none other than The Regency, something Dorinda called “a sh-t prize.”
Harry’s RHUGT appearance might have been brief, but it was a pretty big deal for anyone following the RHONY O.G.s.
Who is Harry Dubin?
Sonja previously described Harry as conversational and charming “when he wants,” something which Dorinda fully agreed with on a RHONY Season 11 After Show.
“He has a trust fund,” said Sonja in the 2019 interview. “Like some other people we know. So, he goes out, and he’s looking for a good time. Too much time and too much money … And he is very charming and fun. He’s great to have around as long as he’s not trying to date you.”
Dubin's late father was a self-made man who started as a door-to-door Bible salesman and eventually became one of the biggest real estate developers in the D.C. area, according to an obituary viewed by The Daily Dish.
He and his brother both went into business, as Louis Dubin, is a high-profile real estate magnate with acquisitions worth billions of dollars.
Harry was introduced to RHONY as the former husband of Aviva Drescher, who appeared on Seasons 5 and 6. The couple divorced in 2005, several years before she became a Housewife, and share a son together.
It was later revealed that, years before marrying Aviva, Harry dated Sonja when they were both in their 20s and he was living in Washington D.C.
On Behind the Velvet Rope with David Yontef in 2020, Harry explained he came upon Sonja dancing and learned she was staying at the Park Hyatt Hotel. He only got her first name, and as there are multiple Hyatts in the area, he “scoured the city” until he found her.
They ended up at a jazz bar before Sonja brought him back to her room and bathed him, as he told it.
“It was great. To this day, I tell her that,” Harry said in the interview.
Eventually, he went on to marry Aviva.
“We’ve been very close since then,” Harry said of Sonja. “I have the utmost respect for her, and I love her to death.”
Harry and Sonja’s romance was briefly rekindled on RHONY Season 6. Harry said he wanted to “take it to another level,” claiming he was “totally serious” about their future. He even presented Sonja with a beautiful ring under the pretense that it wasn’t an engagement ring but “a step to that.”
“This is just a ring to tell you how much I love and care for you,” said Harry.
“Nobody knows me better than Harry,” Sonja told producers. “He’s charismatic; he cracks that grin of his; he’s wearing his cute velvet jacket. I have to admit, the possibilities are endless.”
But the two soon broke up, and Sonja later changed her tune. Sonja even said on Watch What Happens Live with Andy Cohen in 2019, “Harry’s like an itch I can’t scratch, but I can’t stand him because he’s a f-ck up.”
The Housewife also alleged Harry cheated on her.
But she wasn't the last RHONY woman to be linked to Harry. On RHONY Season 6, it was rumored Luann also had something going on with Harry. The pair met at one of Sonja’s cocktail parties in the early 2000s and, as Harry stated in the Velvet Rope interview, Luann pulled him into the taxicab, and they “had a very nice time.”
“That’s the way Luann is,” Harry said in the 2020 interview. “She goes after what she wants, and she gets it. You can’t really deny that.”
He also claimed it was just a “one-time thing.”
Then, in 2018, headlines caused whiplash when Harry and Ramona were photographed making out at the Pomona restaurant in Manhattan.
It was quite the change of heart since, just one year earlier, Ramona said on WWHL that she would never date Harry, despite him being “extremely charming and personable and fun to be with, and he’s kind-hearted, warm, and generous.”
Ramona also said she hadn’t dated Harry in the past.
“Oh my god, I was repulsed!” Sonja said when learning of the kiss. “I mean, I don’t want to make out with Ramona, and I don’t want Harry making out with Ramona.”
She added, “I’m not mad at Ramona, but I am so upset with Harry.”
The kiss came back to haunt the women in 2021 during a girls’ lunch on RHONY Season 13, to which Sonja playfully rolled her eyes.
For her part, Ramona said she and Harry were “just friends,” adding Harry “gets a little frisky.”
Harry was also associated with Tinsley Mortimer and Kelly Killoran Bensimon. Back in Season 9, Harry told Tinsley’s mother that he knew Tinsley for “a very long time,” and Carole Radziwill half-wondered if Tinsley would be next to ride the Harry train.
Tinsley, though, seemed less than interested.
“I met Harry Dubin when he was hanging out with Kelly Bensimon in Miami,” Tinsley said at the time. “And now I find out he’s been with Sonja, Luann. The guy gets around, but I would not touch him with a 10-foot pole.”
In 2020, Aviva said on the Out in the Wild podcast that her ex dated Kelly outside the series “somewhere in the past few years.”
“I’m not surprised because, I think, at this age — late 40s, early 50s — I think that there’s probably very few single nice men out there,” Aviva said.
On RHUGT Season 4, Episode 5, however, Kelly put to bed any rumor that she and Harry ever hooked up.
“I have not made out with Harry,” Kelly said with a smile. “Would Harry like to make out with me? I’m sure.”
We couldn’t say we’d be surprised!
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