Dorinda Medley on Grief, Identity and The Real Housewives: ‘I was angry. I was lost. I felt like I got cheated.’

0:00I think reality TV is very different now. You know, there's a lot of influencers. It's a lot more curated. You know, we were like raw footage, let's face it. And I think our audience trusted that we were exactly who we are and we're authentic. So when people meet me, they always say, you're exactly like we thought you would be. Yes. I really haven't dated a lot of people. I was the marrying girl. Hello and welcome to How to Fail with Elizabeth Day. This is the podcast that's all about reclaiming and reframing failure, not as something to be ashamed of, not as something that defines us, but as something that we can learn from that might be a lesson wrapped up in a mistake.

0:55in person, on the phone, or using the award-winning app. It's nice knowing you have help finding coverage that best fits your needs. Like a good neighbor, State Farm is there. My guest today is a woman who became a reality TV star, not by being perfect, but by being real. Dorinda Medley is best known for her six unforgettable seasons on The Real Housewives of New York, where her wit, warmth and iconic catchphrases made her famous. Whether she was making it nice at her beloved Bluestone Manor or telling Sonia Morgan to clip it, Medley was never afraid of showing her flaws and that arguably was what made her so compelling to watch.

1:39But before the glamour and the gifts, she lived many lives. Born and raised in the Berkshires, Massachusetts, she started working in fashion after graduating from college. She relocated to London with her first husband, a Scottish banker, where she launched a cashmere line. Her clients included the late Princess Diana. After a decade abroad and a divorce, Medley returned to the States as a single mother. A second marriage to DC power broker Richard Medley was tragically cut short when he died after only six years of their being together. Signing up for The Real Housewives in 2015 was a radical act of reinvention and one which catapulted her into popular culture.

2:24Since her time on the show, Medley has published a memoir starred in two seasons of Ultimate Girls Trip and was recently on the US Traitors. She also co-hosts a daily radio show, Reality Checked, on Sirius XM. Being on television has reinforced two big things for me, Medley once reflected. 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. Dorinda Medley, welcome to How to Fail. So happy to see you. And I have to say, I sound so much more important with that British accent. I feel like I'm on BBC. It's so good.

3:06Oh my goodness. Thank you so much. Isn't it interesting how when we listen to others talk about yourself, it's both incredibly warm and also a tinge of sadness. I don't know why that is. Yes. Well, I suppose sometimes it might sound a bit like a eulogy. Maybe it's that and it's just pulling you back into those moments and with your voice so melodic. It's like, well, yeah, I know that girl. Well, not only do I feel I know you through the medium of reality TV, but I'm lucky enough actually to have gotten to know you. And I have to say that you are even better in person than you are on screen. But I wonder what most people say to you on the street when they recognize you.

3:48What's the number one thing that people say? You make it nice. No, I know what you mean by that question. I think the thing, and I think that's one of the reasons why our cast did so well, is we were authentically ourselves. We went on, and I can say that wholeheartedly. If you see Luann and I out, you will literally say they're exactly like they're on TV. So we didn't come on TV to present you with our personalities or present you with something and, you know, create these personalities. They're there. So I think I read recently that authenticity is far more powerful than love. Oh. Yes. You know, because authenticity has staying power.

4:34It creates nostalgia. It's something that creates, you know, a feeling of warmth and safety, right? Trust. And I think our audience trusted that we were exactly who we are and we're authentic. So when people meet me, they always say, and just stop a little bit of my cat, you're exactly like we thought you would be. Yes. Obviously, it's a little bit more on steroids when you're on TV. And there is the edit. Not that I ever blame an edit, but, you know, it is reality TV. But pretty much, you know, I'm a character. Luanne's a character. Sonia's a character. And we really are those people in our lives.

5:10Do you ever regret having been too authentic or too real, too honest about yourselves? Because I imagine you forget the cameras are there after a while. Yeah, absolutely. I think in order to, I think people don't understand that the cameras aren't just there for the scenes you see. There's sometimes we fill six, eight hours a day. And especially on the girls trips, we're filming from eight in the morning to 11 at night. Wow. So you do forget. But I think to be unaware of the camera, I think to sign up for reality TV is you have to just take that mask down of everything we learned in kindergarten, that great book, and just say, here it is.

5:47You have to take the mask off and say, I'm not going to think it too much. I'm just going to say it, right? Yeah. What do you think that reality TV has taught you about failure? You know, it's so funny when you asked, when I got that email yesterday and you asked me that, I couldn't, usually I'm very quick on my feet. What are your successes? What are your regrets? What would you tell your younger self? I could just banter it off. But that word failure was really, it kind of took me back at first when I got your email, right? Because I'm thinking, huh, like that's not a word that I have allowed to really be in my life because failure to me equals fear.

6:27Fear equals failure and failure and fear mean you can't do it. So, but I also am hypocritical in saying that a lot because my failures have really helped me to, you know, pick up and get stronger and turn my failures into learning lessons, saying, oops, that didn't work. And within that failure, it has taught me to be very clever about my pivots. Yes. Well, that is, you are amongst friends here because that is the total premise of this podcast and you've put it so beautifully. I hadn't realized until I researched this interview that it was only four years after Richard died that you started on Roni.

7:10Yes. Do you think you were still grieving? I know I was still grieving. And more than grieving, I was sort of like, I always say, I was like a toothpick in the ocean. You know, here I was almost, you know, 50 years old. I'm not a huge believer in just luck. I find it a bit frustrating when people say, I can't believe that happened, because I'm very much of a follow the breadcrumb person. I mean, I think I would have been a great CIA agent, you know, and I always say to people, you know, if you plant tulips, don't be angry when roses don't show up. So I'm really about planting the garden, having the patience for the garden to grow, providing the garden with what it needs so I get what I planted.

7:59And strangely, I've been like that for a very long time, Even when I was dating, when I first came to New York, I realized a couple of things. That I was clever, that I was good enough looking, and that I was social. Like I had a bit of, my mother always said, Dorinda Medley, you have one, Dorinda Sincala, you have something going for you, you have charisma. And when you walk in a room, you will be noticed. So if you're good, you're going to be great. If you're bad, you're going to be terrible. And I remembered that. And I did always know that I had something that people would pick me out or want to talk to me.

8:35And when I came to New York, I was very curated about what I did, who I dated. And it wasn't a form of snobbery. It wasn't a form of social climbing or gold digging. I knew from an early age that in order with really no money, no contacts coming from a small town in Great Barrington, that I could have been the girl that married the wealthiest man in my town. But somewhere along the journey with the help of my mother, who always has had such a big belief in me and her children, but especially me, I always think about that now and I write about it in my book, is that I needed to do, I had to be very careful about my choosing because each step was going to mean I didn't have to go back to the Berkshires.

9:26So I kind of didn't date certain people because I was like, that's not going to be a good father. That person has problems that I don't want to take on in my life. I had sort of what I thought was my vision board of my life very early on. Now, Now, of course, the vision board has been taken down and scribbled on and stamped on. And that's okay. I got new pen and paper and different color crayons, right? But I kind of had a set belief in myself and my vision board very early on. So you were planting these seeds. So when Roni turned up, we started this conversation talking about how you were still grieving when you did it.

10:06But was there something about the offer? All of a sudden, I kind of at marrying Richard and just really experiencing total accepting love, because I really didn't date a lot after my first marriage, because I was then very focused on Hannah. And I was like, well, I got divorced. Yeah, Hannah, my daughter. I was like, well, I got divorced. She didn't. So we cannot now rock the apple cart and start bringing in a lot of people in a lot of situations. I need her father present. And I always believed, maybe it's very old fashioned, but when you start to bring other apes into the jungle, like it causes problems.

10:45So I was like, her father has to be still the number one man in her life. So I had never even had anyone sleep at my house ever the whole time I was dating after I divorced her father. And Richard came along and he just was like, he fit all the marks. He was accepting of me. He was accepting of my situation. He was accepting of my hopes and goals. He was accepting of Hannah wholly and purely and what I could. And he was accepting of what I would allow her to be. Like you couldn't have me unless we come as a unit. So I kind of remember at one point, I truly remember this because here's a secret.

11:23I had a big wedding at the Four Seasons and I got married at Brick Church and we were at the Four Seasons Fountain Room. I had been married like a month after he got engaged to me because, and we literally went down to town hall and got married and really did a sex in the city, had lunch at a diner with my parents. Because I said to Richard after we got engaged, he said, okay, now you can move in with me and bring Hannah. I was like, oh no, no, no, no. That's just a ring. Like if we got to make this shit legal, if you will be. So he said, fine. He said to me once, you're like a, like a crazy horse in a stable that just keeps kicking the door down.

12:00Just let's go down to town hall and do it. So, and then I moved in with him. And I remember after we did that, knowing the secret, we, very few people knew. I thought, Dorinda Medley, now Medley, you have figured it out. All the way from Great Burrington here, you are in a beautiful townhouse, a wonderful husband. He's successful. He's stable. He loves my daughter. Like I really was like, God damn it, girl. You did it. You got to the top of the mountain. You are there, right? This was the vision board. This is the vision board. Look at me. I was quite chuffed about myself. Take six years later, I'm back at the bottom of the mountain again.

12:41Hannah's gone to college. I am that much older. Richard's burying a husband. And I'm almost turning 50. I'm thinking, really? Now what? because the two kind of, for me, most favorite labels, if not three, mother, my husband and family was kind of gone in one year. Right. So I took some, you know, I kind of reconnected, not that I ever disconnected, but really kind of went back, did my morning, kind of was thinking, what do I, like, am I too young, too old? Do I start? What? Like, it was that weird thing. I was too young, too old. Like, do I start another, like what, you know, do I sell Blue Storm?

13:23Where am I? Like, it truly was like, like, what? So, you know, Ramona was always, was a very dear friend, Luann and all of them. I always stayed in contact with them. And, you know, they had asked me previously to be on and I would always be in the background and scenes. I don't know if you look at that. Yeah. Don't you worry. So Ramona said to me one day, enough, like you need to do something now. And, and, and, you know, it would be great. You'd be great at housewives. I mean, you don't with everybody you've been on and you know us and just just do housewives for a year and do something because and I thought you know what uh I she said you can be a friend you can be a friend and if you don't like it you can leave it's four months four months of filming right and I thought so I think I kind of did you know I it's so funny because now it's much more of a bigger process I had lunch with Ramona and Lisa Shannon or it wasn't even Lisa Shannon one of the people and And they were like, okay, you can be on.

14:21It was that simple. I don't remember thinking of it as auditioning. I'm thinking of, I'm going to do this. And your life changed and so did ours as viewers. And we're going to come back to Housewives as it pertains to one of your failures. But your first failure is playing Superwoman. And as you put it to me, I played Superwoman so long, I forgot how to be vulnerable and allow outside people to help me. So tell me when you first realized this about yourself. after Richard died. And that's why I could do housewives. It all feeds because I knew that I came to New York City, you know, without a lot of money, a lot of, not a lot of opportunity.

15:02And I was always, I never, I was very careful not to show too many flaws and keep it, you know, and do everything right and follow the rules and never be unhappy, you know, and mourn privately. And, you know, it's not that I was superficial. It's just that I wanted to appear strong. I can do everything. I even remember with Ralph, you know, my first husband, who, by the way, I still love today. And he's a great guy and he's very close to Hannah. And I attribute all of Hannah's, you know, a lot of, not all of Hannah's success, because Hannah owns her own success, but her success, a lot of her success in her life, not just from me, but from both of us.

15:41But, you know, I even remember when we moved to London for the first time, I didn't know a soul. I mean, my best friends were at Peter Jones. I'd go visit people at Peter Jones at the Candled Place. There was that Florio brand, I think it was called. Yes. Yeah. It's still there. I actually had lunch with them at L 'Oreal one day because I just was looking for a friend, Right. And, you know, I just studied how the women dressed and studied how they set tables and took a took a course at the Lee School and really made sure if Ralph had to go to work at 5.50 in the morning, I was up waiting for him.

16:16Made sure I knew when he came home, made sure I laid out his clothes, made sure I took on this investment banker's wife, never looking scared or unknowledgeable. knowledgeable. Like I watched the way lady so-and-so did stuff. I watched the way people, you know, dressed their children when they were in the park. So I became a study of that. And I just always was afraid that I think I could do it. No, there was no, there was no, no. Absolutely. Are you tired? No. Would you throw this? Absolutely. You know, everything was yes, yes. And you know, the truth of the matter is when I look back at that now, I was afraid.

16:52I was young. I had no friends. There was no phones. I couldn't barely contact my family, you know, because there was no cell phones, no FaceTime. There were a lot of times when Ralph was thankfully working 12, 14 hours a day and gone three days a week. And I had a brand new baby that I wanted my mother. Yes. But I couldn't do that. So I didn't reach out to a lot of people and say, and when my mother would call and be like, how are you doing? I'm like, I'm fine. It's great. It's wonderful. We We're going to the Venice. Like it was all that. Yeah. And then now I feel like I'm much more, I'm much more saying, I don't want, that frightens me.

17:33Like, and I need your help. Can I talk to you? I even texted someone the other day. And after I texted, I thought, Oh, should I put that in text? I said, listen, can I, if you get time, can you call me back? I'm feeling sad today. And after I sent it, I kind of, cause I sent a flaw. Oh, Oh, well done for sending the text, first of all. Yeah. And thank you so much for talking about this because it's so relatable. And this is the thing. We connect as humans through our vulnerability. That's it. It makes you more lovable. It makes me feel closer to you when you do me the honor of sharing something like that.

18:08And that's what housewives allied me. So when you go full circle, all of a sudden, because I didn't really give a shit anymore, you know, and I was still grieving, for me, I wasn't great at therapy. I mean, I went to it like three times. I was like, I don't want to talk about him. Like, I wasn't great at it. And I found myself getting very insular and angry. A lot of people mourn by crying a lot and stuff. I was angry. I was lost. I felt like I got cheated. You know, so it was a great way for me to work through my really housewives. And I always thank Andy Cohen for this and the Bravo world. It was really a place where I was able to go through a lot of my mourning.

18:49I met Carol Roswell, who we had that incredible bonding scene with in London. I remember. It opened up a bigger world. And I just was able to be vulnerable and not care. I'm not perfect. I don't always get it right. This is who I am. And I'm going to give you this. You can take it. You can do what you want with it. If you want to love me at the end of it, great. If you don't, that's okay too. But maybe you'll learn a lesson. Both good and bad. Yeah. Do do that and don't do that. You know what I mean? And I'm okay with that now. Yes. Because I have been doing the right thing for a long time. It's like it was your own version of therapy.

19:30Correct. And it came at this very powerful time. As you said, you turned 50. It's like you've had this whole other life. And the great thing about it, there was another turning point I remember. I probably, I had no idea really what fame was or what fame does or how it affects you. remember when the housewives first came out, the first episode came out, and I was down at my fruit stand in my pajama bottoms, because it's a cross street and a hoodie, because I always run down and get some fruit after. And this person turned to me and said, oh my God, is it you? And I was like, I don't know. Where did we meet?

20:06And it just took me by, and I thought, oh no, she knows me from the show. And it was that moment where you really, a veil went down where I realized, now I have given my life to everybody. That's scary. And it was scary. But what it did do is it, people fell in love with me for the first time since I was a little girl, not because I was Dorinda Lynch, you know, Ralph's wife. I wasn't an investment banker's wife. I wasn't Hannah's mom. I wasn't Mr. Medley's wife. I was just Dorinda. Dorinda. Yes. And it was the first time in a long time I was just, they were falling in love with me. Beautiful. Or falling and not in love with me, but whatever it was, it was just all mine.

20:59They were seeing you. Yes. You know, I think that what it did to the housewives, which is really kind of probably a weird thing to hear. it made Richard's death a gift because I was able to give it to the world and take what I learned from it because you know we I was young I was a young widow so I remember a woman saying to me Eli's one day I said oh my god she was like in her 80s and I was having a drink at the barn I said I'm a widow too she goes oh no you're not a widow I'm sorry your husband died but you need a different

21:38I think I was able to give that gift, the gift of A, what I had to go through and B, the fact that I was still a relatively young and vibrant woman to be a widow. And I cannot tell you the women, the people, the community that has reached out to me over the years and still does. So powerful.

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22:42Limited time in participating US restaurants. Richard bought you Bluestone Manor. I know. Bluestone Manor, for anyone who hasn't seen Housewives, is iconic. Basically, Bluestone Manor is the extra housewife in your seasons. It's the Disney of Bravo. It's incredible. It's the Disney castle of Bravo, I always say. And I'm the Cinderella that lives there. It's so incredible. What was it like having your housewife's castmates there the first time? Wow, that was an experience because, you know, I come from when you imagine the first year, I'm still like thinking I'm still a person with, and these are women that are going to have boundaries and like not stay with their thing.

23:27Yes, cast. And, you know, execute the sort of social graces you do when you're a guest, right? But then I realized, so of course, I'm very proud and they're going to come here and see Bluestormanna. It's going to be beautiful and I'm going to cook and clean and decorate and make it nice and they're going to respond to it in that way. And when it didn't go that way, I was like, who the hell are these people? Because, you know, in the end, I think we probably created some of our greatest TV. Agreed. up there. We have gone through things. I always love about Bluestone Manor because it's on 18, 19 acres.

24:04You have to go through a gate in a long driveway. So when you are up there, you're there. Like you're there, there. So what happens? And even off camera, the shit that happened that you guys didn't see. But all I know is we'd all wake up in the morning, whatever disasters were happening the night before, somehow we all got our shit together and we were all back on it, kind of, you know, sharing our French toast, doing the next thing. That was the great thing. Like we were able to create this great TV and have our arguments, but somehow get right back on the horse and keep it moving. And we're like that in real life.

24:43If I could show you, I'm on a group text right now with me and we all do, we stay in touch all I'm me, Luann, Sonia, Jill, Ramona. And sometimes I'll just sit there and I think I would never because I, but I could publish these and it's like a show just the way they're not even speaking, they're texting and I can hear their voice and I can hear the disagreements. And then it starts like, let me just give you this one. Something was said yesterday and Luann responded, oh, well, darling. because I could hear her voice. Are you out of your mind or minds, should I say? Oh, this is so amazing. Wait, who sends the longest texts?

25:31Sonia. Okay. Does anyone... Understandably. Does anyone voice note? No. No. We're old school. We're all old. Okay. Does anyone send GIFs? Like hearts? Like heart things? I love you. No, there's like a little video thing, like a meme. No. No, you're just old school. We're very old school. Yeah. I am obsessed. And there's a lot of like, you know, is anyone I'm going for coffee at the Carlisle? Is anyone around? You know, because we've all got to remember, we've been swimming in this. Yes. People don't think, it's not pretend. We've all known each other for a long time. We've been through marriages and divorces and children and baptisms and parties after parties.

26:17Yeah. I mean, there was a time in New York where we only really, because the downtown was kind of off limits. It was a little bit more scary back in the late 80s and early 90s. And so everybody really existed on the Upper East Side because there was not as many wandering places as there are now. Just like London, you know, it's gotten much more expensive. So at any one night, you always ran into everyone and we all went to the same five cocktail parties. I love it. I love this for you. your second failure is about housewives so it is that in the beginning you got too emotionally and sometimes physically too upset about the negative feedback from trolls and haters it was terrible the first time I finally did something that uh you know because in the beginning everyone's like oh we love her she's so great they're in the mouth he's fantastic so of course I'm like yes sake they love me yeah like queen of paltrow at the oscars and then the haters and the trolls start to see but then you have a bad episode and and i remember just like getting obsessed with these comments and physically feeling unwell and breaking out in hives and thinking oh my god like and it's and it's so fast and it's so furious and you can't it's one of the first things that you have no control over you can't even explain yourself because it's out there in this universe that you don't even know about and you think it's you at the time think your life is over and it's going to define you for the rest of your life even if the things aren't true some of them, someone called, you know, you know, we love and, you know, Dorinda on stairways.com, you know, whatever, it said that you're this person.

28:07And then 92 people have replied to it. And you're like, you're like, so, and what I loved about it is I remember talking to Luanne about it one day. She goes, oh, darling, no, no, no, no complaining, no explaining, who cares? You know, so I really had to learn to share. And these housewives are great because no matter what happens, they don't care about what Charlotte and Cincinnati says. You know, they really don't. They're like, as Sonia would say, well, I didn't know her yesterday. I'm not going to know her tomorrow. You know, they're just very good at like focusing on the good because I'm such a perfectionist in a lot of ways.