Even though the show is called Real Housewives of New York City, none of the cast members are actually wives. But that doesn't mean that viewers haven't witnessed a lot of relationship ups and downs throughout the show's eleven seasons. This also includes the Real Housewives of New York love triangles, and even one or two love squares. New York is a big city, but it seems like these women are in a small social circle, especially since there is a lot of romantic overlap within the cast.
Sonja Morgan reminded the viewers of this during the cast trip in Miami on the May 29 episode. Tinsley Mortimer and Dorinda Medley broke the news to Sonja that Ramona Singer was spotted making out with Harry Dubin. That was the last thing that Sonja needed to hear while she was well into vacation mode.
Harry has appeared on Real Housewives of New York City many times throughout the years, as a love interest of more than one cast member. However, as everyone on the show (aside from Ramona) has acknowledged Sonja is the one who got with him first.
She dated him seriously during the pre-Real Housewives era before rekindling things with him in front of the Bravo cameras. Needless to say she was shocked when Tinsley witnessed the Harry and Ramona's makeout session. However, it really isn't that surprising. There have been quite a few love triangles on this show.
Harry Dubin + Sonja Morgan, Ramona Singer, Aviva Drescher, & Luann de Lesseps
This is the OG RHONY love triangle. Sonja gave a very brief overview of their history during a March appearance on Watch What Happens Live with Andy Cohen, in which she discussed her history with Harry. She summed it up like this:
"We dated thirty years ago. He cheated on me. I broke up [with him] over that. Then, he married Aviva [Drescher]. She threw her leg. He came back to me and I went on a picnic with him on my show."
If only it was really that simple. Aviva is Harry's ex-wife and the mother of their son Harrison. She was a full-time cast member on Real Housewives of New York City from Season 4 to Season 6. During Season 6, Harry gave Sonja a promise ring during a picnic. It's unclear what he actually "promised" her since he ended up abandoning Sonja later that episode to get into a car with Luann. They never explicitly confirmed that a hookup went down, but there have been plenty of allusions to it on the show and off for many years.
And now here we are in Season 11 with Ramona and Harry flirting up a storm before their very public makeout session. Unfortunately, that was not filmed for the show. However, there were plenty of cameras present and TMZ shared photos of Harrry and Ramona in December 2018. Will this "love" story continue past this episode? That's not clear, but it's definitely not the last time we will hear about it. This will for sure be mentioned in another episode and at the Season 11 reunion.
Tom D'Agostino + Luann de Lesseps, Ramona Singer, & Sonja Morgan
Harry might be the first guy who infiltrated the RHONY cast, but he wasn't the last. No one will ever forget Luann's short-lived mariage to Tom D'Agostino. Still, during Season 8, Sonja revealed that she and Tom had been "friends with benefits for over twenty years" during a group dinner with the entire cast. And yes, there was overlap with his Luann relationship. Luann did not care though. And Sonja actually seemed pretty chill about it as well.
But there's more! Ramona also copped to going out on some dates with Tom. Tom even appeared on Season 1, attempting to hit on her while she was at a restaurant with a friend. Tom's time on the show was short-lived, but it will live on forever in all of our brains.
Red Scarf Guy + Bethenny Frankel, Carole Radziwill, & Ramona Singer
This one is a bit of a stretch, because no one actually got in a relationship with Brian Krauss, better known to fans as "Red Scarf Guy." During a Season 10 episode, Ramona, Bethenny, and Carole Radziwill were all drawn to him at a speed dating event.
The matchmaker in charge of the event intended to set him up with Carole. However, Ramona jumped into flirt it up with him and she bought him a drink. This encounter resulted in a case of "she said, she said" between Carole and Bethenny, who both exchanged numbers with him and texted him afterward. However, they both had very different stories about those interactions. Cutting to the chase, Bethenny claimed that she fixed him up with Carole and "passed him along" to her. Carole insisted that she made her own moves to connect with him and that Red Scarf just wasn't interested in B.
This story is far over though. Red Scarf is in the Season 11 trailer and it looks like he's on a date with Ramona!
Honorable Mention: Gary Brody + Ramona Singer & Jill Zarin
This did not happen onscreen, but it is just another example of the small pool of guys in this social circle. Real Housewives of New York OG Jill Zarin is currently dating Gary Brody. But during the Season 10 reunion, Andy Cohen confirmed that Gary used to date Ramona. It really is a small world.
Honorable Mention: Adam Kenworthy + Carole Radziwill & Luann de Lesseps' Niece
This one isn't a love triangle among Housewives, but it might as well have been. Luann was very invested in this situation. Her niece previously dated her then-chef Adam Kenworthy before he got together with Carole. Luann and Carole feuded about this from Season 7 to Season 10.
No one can blame any of these guys for having an interest in the fabulous New York Housewives. However, it's hard to see the appeal in dating a guy who has dated your friend. Many times over. But when it comes down to it, these love triangles, love squares, and love pentagons make for great TV.