Exclusive: Dorinda Medley Says ‘Yes’ — On Her Terms

Dorinda Medley is on a roll. Yes, in her life and career certainly, but, in this case, I’m referring to Medley’s 90-second articulate, rapid-fire, eye-opening monologue she’s delivering as we embark on a conversation for this story. She ends her epic recitation thusly: “Look, when I was good, I was great. When I was bad, well…” she says, throwing her head back laughing with the entirety of her being in one joyous, graceful motion. That clincher of a line this indisputably formidable woman uttered could be referring to her life, her career, her daily mantra or her autobiography title. After all, the Berkshires born and raised Bravolebrity is certainly known for her memorable zingers (“Not well, bitch!” anyone?). Luckily for me, today, this very moment, Dorinda Medley is good, oh so very good. And she came to play.

Medley, of course, became a household name after her era-defining, half-decade run on The Real Housewives Of New York City where—it must be said—she and Bethenny Frankel were the decided standouts in the appealing cast of frenemies. To watch Medley and Frankel navigate conflict and ultimately find resolution was not unlike witnessing two world-class heavyweight champions respectfully assessing their daunting rival. By contrast, when Medley and castmate, socialite Tinsley Mortimer, fell out badly, it was nearly too cringe bearing witness to Medley routinely annihilating the grossly over matched Mortimer. Medley respects forces of nature, as she’s one herself. Mortimer never stood a chance.

In some ways, Medley’s 2015-20 star turn on RHONY seems like a million years ago. Her contribution to Andy Cohen’s zeitgeist-loving creation isn’t insubstantial in the only currency Bravo fans understand: being memorable. “I made it nice!” “Clip! Clip! Clip!” and the aforementioned “Not well, bitch!” are the stuff of legend at BravoCon (it’s exactly what it sounds like). I mean, which Upper East Side housewife delivered more quotable moments than Medley during her cut-through-the-noise stint on the show? Not a one.

A decade ago, my oldest friend Greg Calejo, co-founder of Amplify Partners, a powerhouse Manhattan-based luxury brand marketing firm, introduced me to his dear friend Medley at a chic downtown cocktail party. (Back then you knew the shindig was chic when the after party was in the Meatpacking District at Soho House). “My goodness, you look like Princess Di!” were my first words to Medley. She laughed, hugged me hello and said, “I used to hear that all the time when I lived in London.” London? I thought. There’s a story there. I wasn’t wrong.

Dorinda Cinkala was born in Great Barrington, MA to parents John and Diane. After graduating from Franklin & Marshall College she moved to NYC to work for Liz Claiborne. In Gotham, she met and married her first husband, Ralph Lynch and had daughter Hannah. Later, in London, she launched the cashmere brand DCL Cashmere. After ten happy years abroad, our heroine returned to New York City to work as a real estate agent, marrying the love of her life, hedge fund advisor Richard Medley in 2005 a mere six years before his passing at 60. The same age, not insignificantly, his widow will be celebrating come December.

By the by, Medley looks terrific. When I mention this to the Tuesday afternoon host of SiriusXM’s Radio Andy, best-selling author of Make It Nice and owner of Bluestone Manor Bourbon, named after her iconic almost-castle in Great Barrington, it launches her into action. Strap in, folks.

“Someone told me at a bar recently that I shouldn’t tell people I have a 30-year-old daughter because people believe I’m still 45,” Medley starts, gathering speed and ferocity with every syllable. “And I said, ‘Why would I possibly want people to believe I’m 45? I own every single year, space and period of my life. And each one has brought such wonderful things.’ You know, when I was in my 20s, I was getting married and having Hannah—and I love that. When I was in my 30s, I was newly divorced, moving back to New York City from living in London for ten years, and had to reestablish myself as, not a single mom exactly because Hannah’s father has always been present, but as someone who was now saying, ‘OK, this is the new me, I’m going to go back to work, I’m going to be raising Hannah, you got this!’ The truth is I left New York City as a child, and I came back to it as a full adult and mother.”

She’s just warming up.

“I love that in my 40s and 50s I was married to Richard and that brought such great things not only for me, but for Hannah. We were united as a family, and a whole different world involving politics opened to us. Richard and the DNC [Democratic National Committee] working and watching Richard navigate through being a speechwriter for so many important people. It was during this time that I’d say I found my stride. In my second marriage, I knew who I was going into it. I look at marriage very differently now. You know, we were an incredible team and after he passed—12 years ago now—this growth period occurred. I watched Hannah go off to college, and my husband passed all in one year. It was a lot, equal parts humbling and reidentifying in every way because all I had identified with since probably even before I was married, was moving to New York, getting married, having a child—making my life and my daughter’s life a little better than my life was as my mother and father did for me. But almost instantly both of my identities—mother and wife—disappeared. I could have shut down or moved right through it. Guess what I chose? Exactly.”

I’m transfixed by her raw, unapologetic passion in recounting her life so succinctly. I asked her what happened next as if I was reading a New York Times best-selling page-turner.

“Well, then, Bravo came along, and most people didn’t see that fit for me,” Medley says. “But for me Bravo was…[Long pause] Listen, being on Bravo wasn’t always easy. I think one thing that made me both a success and made me probably exposed and vulnerable was that I was so authentic on camera. The truth is I love being around great women. Women have always been my friends—and of course my gay male friends as well who are like an extension of me. I once thought the only way to be happy: I had to have a husband. But you know what, some of the loneliest people I know are married. I don’t have to be Ralph Lynch’s wife. I don’t have to be Hannah’s mom. I don’t have to be Richard Medley’s wife—which were all incredible titles to be sure, and I’m honored to have had them. But, suddenly, in my 50s, I started this whole new career, just being Dorinda. Can you imagine? [Laughs] I now know how to make my own money. I’m finally… free.”

At the conclusion of the 2020 season of RHONY, Andy Cohen and Bravo famously put Medley in what they referred to as a “pause” from the show (other former Housewives from several franchises still take umbrage with the term since it wasn’t afforded to them when they exited their respective shows). I ask Medley about being on pause, and her eyes light up and she smiles. “Oh, that… That’ll work itself out,” she says. “I think people love me for being different. And I’ll tell you what, I was made for reality TV because I don’t ever get overly attached: If someone likes me, great; if someone hates me, well that’s OK, too. You know why? I’m very happy with me. I’m very accepting of myself. Always.”

I have to say—and this is something even her detractors must begrudgingly admit as well—when Dorinda Medley is on a television screen, it’s hard to take your eyes off her. But how much do we really know about this public person who lives a kinda-sorta private life? Where did this galvanizing energy force who regularly explodes into our living rooms come from?

“As a child, I used to tell my mom all the time, ‘I never want to grow up!’ Medley says, a little softer in tone with a big smile on her flawless face. “I used to cry to my mother: ‘I don’t want to grow up! I just want to be a little girl forever!’ I never realized it when I was a kid, but my parents being together and in love gave me the baseline to do anything. Funny thing is I still feel like my parents—even now at 85 and 90—I know I could still go home if I ever got in trouble. That safety net of ‘home’ has always been there for me and I’m so grateful for it.”

Over the years of being in Medley’s company—often as a weekend guest at her magical home in GB, Blue Stone Manor, featured prominently in Architectural Digest a couple of years ago—or more often in New York City at some hot-ticket, must-attend opening in downtown Manhattan, we’d often chat about the small stuff that looms large in our respective lives. The fibers that make up our life quilt. One such fiber I loved hearing about involved her time as a waitress at the iconic Berkshires hotel/restaurant/concert venue, Red Lion Inn. I hear she was even “employee of the month” several times.

“Oh, wow! Yes, the Red Lion Inn was the best training I ever had in my life,” Medley says, grinning like a Cheshire cat. “Working there set me up in such a way that no matter what I did after that I had confidence. I started working there when I was 14 or 15. I kept working there throughout my college years and then even after college, when I was in-between jobs, I’d go back.”

What’s the lure of the Red Lion Inn? So many of my Berkshires-based friends mention this place an inordinate number of times. Was this the de facto town square for locals? 

“The thing about the Red Lion Inn being in a small town, is that’s where the famous—at least who I thought was famous—people went to eat and drink,” Medley says. “And rich people. You know, I was the waitress for Barbra Streisand when she came in for breakfast with Jean Stapleton.” What did Streisand order? I demand to know immediately. “She ordered… pastrami!” Medley says, as we both fall back laughing.

“Since we had The Berkshire Theatre Festival and we had Tanglewood so close by, celebrities would find their way to the Red Lion Inn. And Jean Stapleton was just wonderful.”

I then want to know about the Berkshires. So many folks there are adamant that patch of land is sacred, anointed, special—it’s theirs. I ask one of its favorite daughters the question. “Here’s the thing, if you’re from the Berkshires, you’re fiercely loyal about it,” Medley says excitedly. “We’re an exclusive group. And if you don’t get it, we don’t care. We just don’t. Simply put, the Berkshires is an incredible place that has historically been special because so many of the Gilded Age-era homes are up there. The Berkshires isn’t just a country place but has many of the virtues of a vacation place, too. Its residents have always been educated. You never know who you’re going to meet at a dinner party. But folks here tend to be on the quiet side, not flashy. It’s not about dressing up for people in the Berkshires. It’s about creating. People here are very creative and they’re amazing makers.”

Class isn’t over, friends.

“In the Berkshires, we want to be able to release, relax and reset,” Medley says emphatically. “No one’s looking to go to the fanciest cocktail party—no one here gives a shit about that. You know where the most incredible people can be found every Saturday? At the farmers market. You see, the Berkshires has historically been a place—in the early 20th century—where the wealthy settled. It’s also had a lot of shamans. This land is energetically connected—it’s a very special place. And I’m telling you, when I go up my driveway to Blue Stone Manor, I wouldn’t trade that feeling of peace for anything in the world.”

Speaking of Blue Stone Manor, when you’re there it feels at once grander and more intimate at the same time. Many times over the years I found myself meandering from room to room genuinely admiring the tremendous care and time Medley has clearly put in making that once unruly palace a true home. Every detail—down to the tiniest curio—is perfection. Dorinda Medley may be a lot of other great things, but her expert-level design taste is a sight to behold. I love Blue Stone Manor (how could I not?), and like so many other homes, the kitchen is where you can usually find the once and future queen of reality television, elbow-deep in red sauce. And you may have heard, she’s quite a cook, too.

“At nearly 11,000-square feet, Blue Stone Manor was built by legendary architect Stanford White,” Medley says. “He built it to be used, meaning he studied the light, the doors, the walls are hugely open. So, by day you want to be in that sun-filled living room while on a Sunday night, you want to navigate into the billiards room. I believe the house breathes you in and tells you how to live in it. I love Blue Stone Manor because it wasn’t a house, exactly. It wasn’t a building. It was a place to gather for my family and for my friends to heal after Richard passed. It was my place to heal, too.”

For true Bravo fans, Blue Stone Manor—along with Vanderpump Rules’ powerful monarch Lisa Vanderpump’s Villa Rosa in Beverly Hills—are easily the two most recognizable, OTT homes on the network. Medley even hosted the second season of the franchise spinoff Ultimate Girls Trip (Peacock) at her palatial home with eight former Housewives causing delicious drama for our entertainment—and a hefty paycheck for themselves.

Talking money, Medley is decidedly—and impressively—business savvy and, as she says, needs to capitalize right now while “people are still paying attention.” She’s soon headed off for an extended period to fulfill a top-secret television project that will excite her legion of fans (Medley has more than a million followers on Instagram alone). As I write this, only a week into April, Medley’s already worked this month for the likes of Virgin Voyages, SiriusXM Radio Andy and Clorox. Busy doesn’t begin to cover it.

But, as this issue is insisting on finding out from all its subjects: Is Dorinda Medley happy?

“Yes, I’m incredibly happy now, but I’ll tell you when I think was my happiest period in my life: When I lived in London is where I really hit my stride,” Medley says. “I don’t know if there was a specific moment when I realized I was happy, but I remember the amazing feeling of thinking, ‘Wow, you know what? This girl from Great Barrington has come a long way. I’m married to a successful banker. I’ve got a beautiful daughter. I live in a beautiful place in South Kensington. I’m in Hyde Park walking my child in a stroller looking at Kensington Palace.’ So, yeah, how exactly did I get here? A girl from Great Barrington with big dreams. And there I was in London…happy.”

But, eventually, the bubble burst, and Medley found herself back in Manhattan, divorced and determined to make a great life for Hannah. “You know something my mother always told me that couldn’t be any truer: ‘No one gets out of this without a lot of bumps and bruises.’ And she’s right. Lots of bumps and lots of bruises.”

One bump and bruise currently dominating the Bravosphere involves the two-headed monster of the Bethenny Frankel-led so-called “reality reckoning,” holding docuseries producers and networks accountable and demanding similar contracts as their scripted counterparts; and pending lawsuits levied against show producers, the network as well as the affable principal of Bravo High, Andy Cohen, by two former Housewives widely-known as being, shall we say, hot messes on camera. Both former Housewives are now claiming, retroactively, all kind of malfeasance done to them, even while current Housewives have been quick to come to Cohen’s, the producers’ and the network’s defense. I asked Medley her opinion about this uncharted landscape.

“I think that we’re all adults here,” Medley says. “I signed the contract. These [Housewives] are not children, right? These are adults. They didn’t kidnap me to do this. I signed the contract. I always had a very strong and good relationship with the production company. I still do. But having said that, I’m not going to be dishonest and say I’ve always felt warm and fuzzy about them or what they showed. But that’s life. You know, I’ve had my moments where I’ve been like, ‘What the fuck,’ right? But a lot of that was because of my own doing. The truth is, we were not scripted. And I know other shows may be a little more interactive, but we were not. Our show was completely unscripted.”

As we start to wrap, I ask Medley, who’s been multitasking with an assistant as we chat (with her wall-to-wall schedule, it’s likely the only way she can get everything done), about the concept of happiness and what that means to her.

“As a woman, we can be fearful of so many things from aging to menopause to children leaving to being alone to finances—all those things that are both personal and that society puts on us,” Medley says thoughtfully. “And I don’t know why I’m not fearful of any of those things. I sleep great at night. Here’s my secret: I just don’t feel guilty about prioritizing myself. Full stop.”

Oh, what about love? We need to end on love, no? Is Dorinda Medley closed off to the concept of marriage or having another relationship?

“I’m not closed-off to anything,” Medley says, smiling that famous smile of hers. “I’m saying ‘yes’ to the universe, and I don’t know what shape or form that’ll come. But if it comes in the form of love, I’ll take it.”

As we say our goodbyes, I realize that today, at this very moment, Dorinda Medley chose to use her powers for good. And she was right: When she’s good, she’s great. What a woman. Pause indeed.