Dorinda Medley Gets Real: The Breakout Star Of Bravo’s ‘Real Housewives Of New York City’ Spends A Day In Saratoga

The moment Dorinda Medley and I locked eyes—as we were being introduced some seven years ago at a fancy soirée in lower Manhattan by our mutual best friend, Greg Calejo (more about him in a minute)—I felt an electric charge enter my body as I recognized a fellow mischievous, no-nonsense, straight-shooter: This gorgeous woman in front of me was my kind of people, and I wanted more.

Greg, my closest friend since I was 14, who happens to be a big mucky-muck, fancy brands publicist, BFF with countless celebrities and possessor of a BS meter almost as finely-honed as mine, was blunt: “You two—oh boy!—should definitely know each other!” Dorinda looked at me for the first time with that now familiar glint in her eye and wry smile and said, “Let’s do this, Richard!” And have we ever.

For the uninitiated, Dorinda Medley is one of the biggest stars in the fantastical galaxy known as unscripted (reality) television. She’s arguably the best-known current cast member of her massively popular show, The Real Housewives Of New York City (RHONY), on Bravo, reality TV’s Mecca. The network, home to some of the most-watched and buzzed-about reality shows in broadcasting history, including Project Runway, Queer Eye, Top Chef, Vanderpump Rules, Below Deck, Southern Charm and, of course, the defining guilty pleasure shows of our generation (alongside the Kardashians), The Real Housewives franchise. In that dysfunctional/I-can’t-take-my-eyes-off-of-it world of grown-ass women behaving, mostly, abominably, Dorinda is breathing rarefied air. She and a select handful of other ‘Housewives’—NeNe Leakes, Teresa Giudice, Lisa Vanderpump and, the Haley’s Comet known as Bethenny Frankel—have managed to separate themselves from the pack. Not only are they all undeniably alphas—flip any tables lately, Teresa?—but these women also don’t suffer fools, not for a moment. Bombastic conflict with heartfelt resolution is what I love about reality television and, as it happens, Dorinda, this funny, passionate, emotional girls’ girl, has that in spades. But who exactly is this wildly popular Bravolebrity and why, pray tell, is she gracing the cover of saratoga living? I’m so glad you asked.

“I feel like I’ve seen it all and done it all,” says Dorinda Medley. “I’ve really gotten to the point where I’m very accepting of myself.” (Dori Fitzpatrick)

Dorinda Cinkala had a self-described very happy childhood growing up in the Berkshires of her native Massachusetts. After graduating from Franklin & Marshall College, she started working for Liz Claiborne in Manhattan, following through on an early interest in fashion. While in New York City, she married a Scot, Ralph Lynch, and relocated to London where she welcomed a daughter, Hannah, and launched a successful fashion business, DCL Cashmere (said to be a favorite of Dorinda’s exercise buddy, Princess Diana). After a decade abroad and a divorce, Dorinda returned to Gotham to begin life anew as a single mother. In 2005, Dorinda’s life would once again be rocked when she married financier Dr. Richard Medley, a former Washington, DC powerbroker and speechwriter for vice-presidential candidate Geraldine Ferraro. Only a few years later, in 2011, Dorinda’s soulmate passed away nearly devastating her. Eventually, she met her current love, John Mahdessian, owner of Manhattan’s fabled couture restoration operation, Madame Paulette.

Today, Dorinda splits her time between her Manhattan apartment in the sky in tony Sutton Place and her beloved “Blue Stone Manor” in Great Barrington in the Berkshires. Blue Stone Manor is so frequently mentioned and inhabited on the show, it may be the best-known manse (along with Lisa Vanderpump’s “Villa Rosa”) in the Bravo zeitgeist. To know Dorinda is to understand how generous she is, not only with her time, but also her pocketbook, as evidenced by her numerous charitable endeavors, benefitting Beauty For Freedom, Ronald McDonald House, New York Loves Kids, Gabrielle’s Angel Foundation and, now, Saratoga Performing Arts Center’s (SPAC’s) educational programming. Not surprisingly, Dorinda’s philanthropic endeavors are less well known than, say, her previous run-ins with Countess Luann.

So, yeah, Dorinda is notoriously feisty and quotable, quick to anger and just as fast to forgive and forget. Her are-you-kidding-me?, jaw-dropping moments on camera are too many to list here, but some of the best bon mots emanating from her lips include the classic “Not well, bitch!” response she gave to a snarky Candace Bushnell (author of Sex And The City) in the Hamptons, post-brunch, when Bushnell asked how Dorinda was feeling after a fight Bushnell had just witnessed with a castmate; or when Albany native Sonja Morgan kept talking over her, and Dorinda stood up at a crowded restaurant and kept loudly repeating “Clip! Clip! Clip!” as she gestured with her extended arm while opening and closing her hand in the direction of Morgan’s face; or when frustrated by all the pettiness and fighting at Blue Stone Manor, Dorinda epically exclaimed, “I made it NICE!” All of it seems equal parts genius and silly, and undeniably unforgettable. As former RHONY castmate Carole Radziwill says, “When Dorinda’s bad, she’s sooo good!”

A born entertainer, Dorinda takes great pride in being the consummate hostess, and in the numerous times I’ve been a weekend warrior as a houseguest in her stunning Berkshires home (and, yes, I’ve stayed in and loved the “fish room”), I can’t remember a single moment that the experience of being in her presence while there was anything short of joyous; in fact, we were more likely gasping for air from so much raucous laughter. Every detail in her home is perfect, not fussy. Blue Stone Manor is a genuine reflection of its proprietress: classy, beautiful, real. You never want to leave.

“I think it’s very important for women to hear me and believe me when I say, to be in your 50s and 60s is no longer a dirty little secret,” says ‘Real Housewives of New York City’ star Dorinda Medley. (Dori Fitzpatrick)

So, I was curious what Dorinda’s reaction would be when I first floated the idea of her appearing on the cover of saratoga living. “I love Saratoga!” she said. “Richard, are you kidding me? I have so, so many memories of spending endless summer days there with my parents! My grandfather loved the track and we always stopped for ice cream at Stewart’s before we’d head back home to the Berkshires.” Perfect! My clandestine (and exciting) Operation #Dorinda♥Saratoga was now in full effect. We started making calls. As you may have heard, Dorinda is the guest of honor at saratoga living’s “Best Of Saratoga” event at Prime at Saratoga National on Sunday, October 6, with a portion of the ticket sales benefitting SPAC’s educational programming.

But on a spectacular late summer day, I spent nearly 24 hours with Dorinda as the magazine pulled out all the stops in facilitating her very fun “takeover of Saratoga,” as we photographed and interviewed her all over town. Oh, look, there’s Dorinda getting gorgeous at Complexions! In Congress Park at the Carousel! Shopping on Broadway! Sipping martinis at The Adelphi! It was quite a long day (and night) for all of us, but the results speak for themselves.

And now, in her own words, let’s hear from my dear friend, this formidable woman who still gives me that look with a glint in her eye and wry smile and who makes everything and everyone in her orbit better, kinder and, yeah, nicer. Dorinda Medley may indeed love Saratoga, even more so now, but knowing the kind-hearted people who inhabit this great city I’ve come to adore, I can now report that, Saratogians love Dorinda right back. After all, who can resist a reality star who keeps it really real—for real?

Let’s jump right in? What stage of your life are you in?
I was just talking about this to someone and I was saying it’s a funny thing when you spend your whole life creating titles, especially because I consider myself an ambitious woman. I’ve tried to take on these titles—being successful, relevant, well educated, becoming a wife, becoming a mother, exploring, trying to build businesses—and at my age you look back and you’re like, “Wow, I’ve done a lot of these titles.” And when you’re Dorinda Cinkala who grew up in Massachusetts and Dorinda Lynch who lived in Hong Kong, London, Australia and who was married and had Hannah, to becoming a single mom—to Mrs. Medley as I always call it—and a widow, and then to start this Housewives gig…I realized, after Hannah finally moved out and I moved into a new apartment, that this was an exciting and new phase of my life. It’s also a scary time in my life because we’re in a different time now than when our mothers were 55. They were slowing down, waiting for what the next step would be—probably grandchildren and retirement—and that’s not how it is anymore. I feel I have another good 30 years under my belt.

‘Real Housewives of New York City’ star Dorinda Medley enjoys a laugh (and a martini!) at Morrissey’s at The Adelphi Hotel in Saratoga. (Dori Fitzpatrick)

You’re ramping up. It’s now about you—finally.
Yes! I feel it’s all about me now. It’s a funny thing: People are always asking, “Will you?” “Could you?” “Do you?” and I think for the first time in my life, I’m really letting things present themselves and do what’s right for me, as a mother, as a wife—not as a young person trying to constantly push herself into a new position. Now, at last, I’m very comfortable with the world coming to me and knowing the real me.

Your authenticity is palpable, Dorinda, and you come across so naturally. You’re just completely you.
You know, Richard, I feel like I’ve seen it all and done it all. I’ve really gotten to a point where I’m very accepting of myself, the good and the bad. I think it’s important for viewers and to people with whom I engage to know that I don’t want to present myself as perfect. I made a commitment to myself when I started the show that I wanted to come across as seamless. My goal is that when someone meets me, they think “she’s just what she’s like on TV—I can relate to her.” It’s important to always keep it real, because there are days that you feel great, and don’t mind being someone who’s nurturing, giving, entertaining, always traveling and building brands. But there are also days that aren’t so great, and I have to be OK with saying, “Wow, you know what, I’m tired today; I don’t feel like doing that. I feel a little down; I’m struggling with this; I don’t feel like putting on makeup right now.” And I think it’s so important, especially when trying to engage, that the relatability is what people expect from me.

Being on television has reinforced two big things for me: One, that the audience is very forgiving and so is the world; and two, that the audience feels they know you—that you’re a kindred spirit. One of the most powerful moments for me after the first season was when I was at a fruit stand in front of my building getting a banana, and this woman walked up to me and said, “Can I just say how powerful it is that you spoke about Richard and his passing, that you spoke about becoming a widow.” I was considered a very young widow. And one of the things I said the first season was that it’s not a label that fits. Because as a society, we’ve compartmentalized people with the title of widow as someone who’s 80 years old, who’s had a full life with his or her partner. It inspired me so much, because I realized, as a widow at a young 50, I can still be a part of life. What I thought might show weakness initially, actually came out being very powerful. Because I just said it the way I was feeling it. So, I think it’s very important for women to hear me and believe me when I say, to be in your 50s and 60s is no longer a dirty little secret. I embrace it, I’m proud of it. You mentally change, you physically change, you spiritually change. Because in a weird way, you’re in the last quarter of your life. I’m not so crazy ambitious, but yet I am ambitious. I still want to enjoy my life. I’ve given a lot, I’ve seen a lot, I’ve done a lot and I’ve become a bit selfish with my time. I think the best thing you learn in your 50s is the word “no.” With no excuses. I just say, “I can’t do that because I’m tired.” I want to take care of myself. I would rather be my best self for someone than just be present and not my whole self. That wisdom only came with age.

Let’s talk Saratoga. Tell me about your childhood memories.
Oh my god! I have so many great memories of Saratoga! Going to Saratoga was a whole vacation. Even if we were only going for a day trip, it was a vacation. We never had enough money to stay in hotels or anything, but, literally, the day would start at 5am. I remember there used to be a Howard Johnson’s on the way with a conveyer belt of food, and I was completely fascinated by it. On these day trips, I used to get so excited. I remember all kinds of great events in Saratoga. It was where all the fancy people used to live. We’d enter town and drive around and go to the rich neighborhoods and see all the big houses, stop at a museum and have lunch at some local diner. And we’d go to the Saratoga Race Course and see all the jockeys, and you felt like you were transported into a different world. I remember going to this very famous Italian place—Siro’s!—and we’d go with 25 people and on the way home we’d stop at Stewart’s for some ice cream. It was the best day, because I really was transported into a different world. And I could step out of my life for a day and be a part of it. The other thing about Saratoga I sensed and loved was that even though it was a fancy place, it appeared to have an all-inclusive attitude, and everyone was welcome. I loved it.

Do you see any similarities between Great Barrington and Saratoga Springs?
Oh, absolutely! They both have that old, traditional feel. Back then, Saratoga Springs was very connected to Great Barrington, because we had the Great Barrington Fair Grounds, and there was a lot of horse racing, and a lot of the horses that were racing in Great Barrington were also racing in Saratoga. And that mentality of getting dressed to go to the racetrack and the local places—it’s very old school. So, yeah. Similar for sure, but not exactly the same.

Tell me a little about your home, Blue Stone Manor.
So, my great-grandfather came to America from Italy as a very accomplished mason. Back then, Great Barrington was sectored and the Italian quarter was where all the masons lived. My great grandfather had his own mason business, and when physicist William Stanley [whose company was bought by GE] came up and had this beautiful home built by Stanford White, all his men did the stonework. They called it “Blue Stone Manor” because the stone was taken from the grounds. My great-grandfather worked on it, my grandfather worked on it, and they rolled part of the original house down the hill. It’s still on my property line. So, the house had a lot of history for me.

My Dad would drive us by the house, and I would say “One day, Dad, I’m going to get really rich, and I’m going to buy the house for us. I’m never going to get married, Mom and you are going to live there, and we’re never going to leave Great Barrington!” And he said, “Yes we are, princess,” and it became this fabled, “there’s your house on the hill, Dorinda.” So I told Richard this story over and over again, and it was always this house that no one wanted, because it was old. So about a month before I got married to Richard, we drove up to the Berkshires and he said, “Let’s go by that house you like.” And there was no gate there, and we were going up the driveway and I said, “We can’t go in there,” and he said, “Yes you can; this is your house now, and I want you to have something from me that’s not part of our marriage, that’s just yours.” So, a month before our wedding, Richard Medley bought me the house of my childhood dreams.

‘The Real Housewives Of New York City’ star, Dorinda Medley, lives it up in Saratoga. (Dori Fitzpatrick)

What were your impressions of The Real Housewives Of New York City before you joined the cast?
I didn’t come on the cast in a manufactured way. I had appeared in numerous cameos, since I was at all the parties anyway. I didn’t come on slowly. I vividly remember [Bravo Programming Executive] Andy Cohen saying to me, “Do you have any skeletons in your closet? Because they’re coming out. Also, this experience can either make you or break you.” I didn’t believe that; I believe a person makes or breaks you. I think a lot of these women come on and use it as a platform for narcissism and that’s not what it’s about. It can be therapeutic, though, because you can actually work things out and see things more clearly by being on this show.

My biggest reservation was Hannah. What I didn’t realize was how much of myself I’d be exposing. Hannah’s very private, but even she’s come around because she’s seen me grow so much. After Richard died, she didn’t let me go, and I didn’t let her go—it was as if time had stopped. The first season of RHONY was very hard on her—the total loss of control. Now she enjoys the process and knows how to manage it. But I’ll be honest with you: When we’re filming the show, I have that same feeling you have when you go back to college.

What was the biggest surprise after you joined the show?
How it bleeds into all parts of your life. You’re totally immersed. You have to run this job like your personal life. My goal this season is to take the high road; there’s less traffic up there.

How has Bethenny leaving the show affected you?
When I found out Bethenny was leaving, I was sad. I actually wanted to cry. There’s sort of a good old-fashioned aspect to her I love. She’s a true original ‘Housewife.’ It takes a brave and fearless person to do what we do. And the great thing about Bethenny is that off camera, she’s exactly like she is on camera. We’re very good, true friends. And we’re two alphas. The minute we realized we could run together in the pack, there was relief. She’ll always be one of the OGs.

Have your boyfriend John and daughter Hannah changed significantly since you became the darling of reality television?
I think Hannah is proud of me, happy for me. She’s sort of like the unicorn when she comes on the show. She said to me, “Can you just do me a favor and just be Mom to me?”
She’s very respectful when I’m filming. She said, “Do me a favor—don’t get tired out.” For John, the process is very different. He’s had to grow up a little bit. I think it’s really helped him to grow up and take responsibility, and that’s the side of John most people don’t see. He’s very loving and nurturing and protective of me.

What are your thoughts about being on the cover of saratoga living’s ‘Best Of Everything’ issue?
I simply cannot believe it—and I can’t believe I’m going to meet the mayor at the Best Of Everything party! Who would have thought that the little girl from Great Barrington would meet the mayor of Saratoga Springs? I think Saratoga is perfect; and I think saratoga living fits me perfectly, it represents everything I am. It’s completely my brand. I’m also excited about the event on October 6. You know who we should invite? Sonja. Because Sonja is from Albany. She spent her childhood going to Saratoga. She’s very excited, too.

Given this issue’s theme, what do you believe you’re the ‘best’ at?
Entertaining. I’m very good at it; I enjoy it. And I love creating. I love people to feel like they’re totally incorporated in the process.

What’s the biggest misconception about you, Dorinda?
I don’t allow people to know that I’m actually very vulnerable, and I hurt very easily. Usually, what I’ve done in the past is, I retreat, I blow up and then I retreat again. But I’m also very quick to forgive. My mother said to me once when I was young, “You know what, Dorinda? People are mean for two reasons and for two reasons only: either it’s because they’re very sad, or they’re very angry. It’s not about you. It’s about being sad or angry.” And every time I realize I’ve been quick to anger, I realize it’s frustration, and it comes off stunted. Anger is easy. Fear and sadness are hard.

Some parting thoughts about Saratoga Springs?
I think the biggest observation for me is that Saratoga Springs still has its great personality off-season. It’s nice to see it a little quieter, but it kind of has this really nice hustle and bustle, and it’s alive, and people are very committed and devoted to being Saratogians. So, I love the fact that it has a very strong personality and I love that about Upstate New York in general. So, yeah, I love Saratoga. How could you not?

Want to meet Dorinda in person? Come to saratoga living‘s “Best Of Everything” issue launch party and brunch at Prime at Saratoga National on October 6. To purchase VIP or General Admission tickets, click here.

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