RHONY Legacy: Where the Cast’s Friendships and Relationships Stand Before RHUGT

Fans of The Real Housewives of New York City can expect temperatures to rise in St. Barts now that the former Housewives have arrived at their destination.

The long-awaited The Real Housewives Ultimate Girls Trip Season 4 brings Dorinda Medley, Kristen Taekman, Luann de Lesseps, Kelly Killoren Bensimon, Ramona Singer, and Sonja Morgan back together on the French-speaking island, a welcome-back for the latter three who’d visited St. Barts in RHONY Season 5.

Ahead of the RHUGT Season 4 premiere — streaming Thursday, December 14, 2023, exclusively on Peacock — we’re wondering if the women’s friendships have withstood the test of time since they were all together. Here is what we’ve uncovered.

Who is friends with Dorinda Medley?

One could only hope that Dorinda makes it nice in the Caribbean, especially when forming and maintaining friendships during the tropical getaway.

The Lady of Bluestone Manor — returning to RHUGT for a second time since hosting the Ex-Wives club in Season 2 — shares the screen with the other women after appearing on RHONY for Seasons 7 through 12. Dorinda has since been “on pause” but stays close with her fellow Housewives.

“And just like that, WE’RE BACK!” she excitedly announced at BravoCon 2023, posting a photo with her new travel companions.

Luann joined Dorinda on the October 22, 2023 episode of Watch What Happens Live with Andy Cohen, where Luann cited “D” as showing up to RHUGT with the best wardrobe and the one who made Luann laugh the most. Looking back at their time together on RHONY, both said they could forgive one another for a series of controversial moments, including Dorinda’s engagement toast, Luann falling into the bushes, and Dorinda’s now-infamous "Clip! Clip!" moment.

Dorinda added she was “feeling lots of love” from The Countess.  

RELATED: Everything to Know About the Pirate on RHONY Before a Possible RHUGT Return

Ramona was also cheering the pair on from the live audience, so it’s safe to assume she and Dorinda are on good terms for RHUGT. In June, Dorinda also posted a laugh-out-loud video of her rolling Ramona around on luggage through the airport.

Quite the change since an August 2021 interview on WWHL, when Dorinda admitted she kept in touch with all the Housewives except for Ramona.

Dorinda also had some nice things to say about her castmates when addressing news that she’d had lunch with Ramona and Luann in a February 2023 interview with Sirius XM Radio Andy.

“The great thing about our cast is that we’re all real friends… we have all been in each other’s lives for a long time,” said Dorinda. “We know each other’s children; they grew up together, and even though the show brings its havoc, we’re kind of like N.F.L. football players. We go on the field, beat the sh-t out of each other, but we always come off and pat each other on the ass and keep it moving.”

Who is friends with Kelly Killoren Bensimon?

Although the women didn’t overlap on RHONY (Kelly was a Housewife for seasons 2 through 4), Kelly told Page Six in September that she was warned about Dorinda.

“Everyone told me to be aware of Dorinda [and] to, like, watch out for her,” said the licensed real estate agent.

Things might have been “not well, bitch” ahead of the RHUGT trip, but it seemed to be smooth sailing, despite the caution signs.

“Dorinda is unbelievable,” Kelly continued to Page Six. “She is such a loyal and incredible friend, and I love her so much. We really, really bonded, and I’m just crazy about her.”

Kelly, the woman who made Scary Island Scary Island, also seems to be on good terms with Sonja, especially since announcing at BravoCon 2023 that she’d love to help Sonja sell her legendary Upper East Side townhouse.

“No auction, I’ll sell it,” Kelly told the live audience. “I will sell that house!”

One could hope things go smoothly for Kelly and Ramona, especially since Ramona — then working for Douglas Elliman — said she would consider working with Kelly, as revealed in 2021 on WWHL.

“I haven’t connected with her yet, but yeah. I could definitely do a co-listing with her,” said Ramona. “I respect her, and I think she’s doing really well.”

Kelly and Luann’s friendship also seemed strong when the pair where spotted in February 2022, giggling while taking a stroll around the city, as published by The Daily Mail. Luann also showed up as a guest on Kelly’s Hey, Guys, Hey podcast.

Who is friends with Kristen Taekman?

Better bring some sunblock for that burn! There seems to be no love lost between Kristen and Ramona ahead of the RHUGT Season 4 premiere.

Fans will probably recall Ramona and Kristen had a major fight in Season 6. Adding insult to injury, Ramona also seriously dissed Kristen in May 2023, telling Page Six that she’d forgotten who Kristen was until casting for RHUGT Season 4 began.

“I just genuinely forgot who she was,” said Ramona. “Well, everyone did.”

Kristen clapped back by posting photos of the pair at a Hamptons-based event, reminding Ramona that she’d invited her to a party.

In other words, Kristen came with receipts! So, we’re wondering how that will play out in the upcoming installment of RHUGT.

As for  Kristen and Dorinda — despite having their spats in the past (like when Dorinda went off on Kristen after accusing Dorinda’s boyfriend of being “touchy-feely”) — it's unclear if there will be some tension on the Caribbean Sea’s horizon.

“It’s very interesting, you know Kristen made her return,” Dorinda told Access Hollywood in November 2023. “Old Kristen was very timid and sweet, but Kristen’s got some little nails this time.”

Kristen and Kelly, however, put their best high heels forward on Nov. 13, 2023, serving a slow-motion strut and asking fans, “Are you ready for it?” on Kristen’s Instagram.

Safe to say, things probably ended on a good foot between the friends, who never appeared as Housewives at the same time onscreen.

RELATED: Watch the RHONY Legacy Cast Show Off Their Best Dance Moves and Bikinis in St. Barts

The now-L.A.-based mother of two has certainly kept in touch with some of the RHONY crew over the years and was even spotted with Luann at a charity event in the Hamptons hosted by former RHONY cast member Jill Zarin. 

Who is friends with Sonja Morgan?

We’re not expecting any crazy turbulence between Sonja and Luann, especially since their hilarious fish-out-of-water series, Luann & Sonja: Welcome to Crappie Lake, premiered in the summer of 2023.

In a July interview with In Touch Weekly, Sonja said her relationship with Luann — whom she’d known since before RHONY premiered in 2008 — was akin to “an old married couple.”

“Andy Cohen said it best: In the best franchises, the girls really are friends,” said Sonja. “We have a trust level.”

Luann also spoke with In Touch about their friendship when promoting Crappie Lake, pointing to signs that only sunny skies were ahead for their upcoming ultimate girls’ trip.

“I saw a producer last night who said, ‘You girls are the best because you have your fights, but you’re funny, and you’re not after each other’s livelihood,’” said Luann. “There’s drama and bickering, but it’s not dark.”

Both gave cozy and friendly vibes in an Oct. 21, 2023 “Winter is coming” post when posing in front of New York’s Catskill Mountains.

Kelly, Dorinda, and Ramona all showed Sonja and Luann their support for the premiere party for Crappie Lake. A quick look at Sonja’s Instagram also shows her, Luann, and Ramona participating in a ton of social and fun activities over the years.

However, the Crappie Lake stars might be in hot water with Ramona for RHUGT, especially since telling Andy Cohen on WWHL in July 2023 that the woman who coined Turtle Time was “the rudest to fans.”

Sonja and Kelly seem to be close: In October, Sonja and Kelly graced Instagram with this super-fun selfie, with Sonja wearing a bra while showing off her long locks.

In 2021, Dorinda shared a series of photos showing her and Sonja’s emotional reunion from the Ultimate Women’s Expo in New Jersey, just weeks following the end of RHONY Season 13.

“When you unexpectedly run into an old friend!” Dorinda captioned. “I miss you, too [Sonja].”

Who is friends with Luann de Lesseps?

The “Money Can’t Buy you Class” cabaret extraordinaire said she had “the best time” at BravoCon 2023 with her RHUGT Season 4 co-stars.

“This is what happiness looks like,” Bravo’s official Instagram commented.

Luann, as mentioned is close with Sonja still, and seems to regularly spend time with Dorinda, too. While it’s been a few years since Luann and Dorinda shared the screen on RHONY, the two seemed happy as clams in September 2023 when attending the U.S. Open and posing under the Unisphere of N.Y.C.’s Flushing Meadows-Corona Park.

“I love how generous you are and how real you are,” Luann told Dorinda on WWHL. “That’s why you’re a great Real Housewife.”

Dorinda returned he favor, noting what she loves best about Luann was how “she teaches you how to enjoy life and let things go, and just don’t worry about it.”

Over the summer, Luann also spent some quality time with her former castmates, such as when they experienced the RiseNY amusement in Manhattan and when Dorinda and Ramona joined Luann for her cabaret tour in Texas.

We'll have to see how these relationships change on The Real Housewives Ultimate Girls Trip. The first three episodes dropping Thursday, Dec. 14, 2023, exclusively on Peacock.