Lovett or Leave It Presents: Bravo, America! (with Dorinda Medley)

Summary

Lovett or Leave It Presents: Bravo, America!

Guest: Dorinda Medley

Date: November 11, 2025
Host: Jon Lovett (Crooked Media)

Main Theme

This episode of "Lovett or Leave It" brings together pop culture and politics, exploring the overlap between reality TV dynamics and the current political landscape. Jon Lovett sits down with iconic Real Housewives of New York cast member Dorinda Medley for an honest, funny, and revealing discussion about fame, authenticity, and what politicians could stand to learn from the world of Bravo.

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Key Discussion Points & Insights

1. Reality TV & Political Parallels

• Attention-seeking in Politics:
  • Lovett positions reality TV as an essential lens for understanding modern politics. He quotes Congresswoman Sarah McBride:

    “Some of my colleagues are treating me the way they are treating me...because they want attention. They want to employ the strategies of a Bravo TV show to get attention in a body of 435 people. And the way to do that is to pick a fight with someone and throw wine in their face.” (01:39)

• The “Bravo-fication” of Congress:
  Both host and guest discuss how the chaos, drama, and tactics of reality TV are mirrored in the strategies of politicians vying for attention.

2. Dorinda’s Reality TV Beginnings

• How Dorinda Got Cast:
  • Dorinda recounts being introduced to RHONY through friendships with the original cast, particularly Ramona Singer, and initially turning down opportunities because of family and her then-husband’s political work.

  “At the time...I just wasn’t in a position where...I wanted my daughter on TV so young.” (07:21)

  • Eventually, after her husband's passing and her daughter leaving for college, Dorinda joined and quickly felt at home on camera.

  “I remember that camera coming around and thinking, oh, I like the camera, and I think the camera likes me.” (08:14)

3. Vulnerability, Grief, and Authenticity

• Therapeutic Power of Reality TV:
  • Dorinda describes joining RHONY as being at a personal crossroads—having lost her husband and sense of identity, the show gave her purpose and connection.

    “For so many years, I’d been...Hannah’s mom, Mrs. Lynch, my first husband’s wife...It was really interesting to all of a sudden just be Dorinda.” (11:22)

  • Opening up about her widowhood and grief, Dorinda acknowledges how being vulnerable onscreen resonated with viewers coping with their own losses.

    “It was a teaching moment as far as I’m concerned.” (22:28)

4. The Game of Reality TV

• Strategy, Authenticity, and Editing:
  • Dorinda describes reality TV as “chess in high heels,” where strategy matters but authenticity is ultimately rewarded.

    “I’m kind of in life always playing chess...But it gets exacerbated a bit when you have the cameras on and you’re filming 12 hours a day.” (14:18)

  • She notes the learning curve in handling confessionals and editing, praising Bethenny Frankel’s confessional skills.

  "There’s nothing like a Beth Frankel confessional." (13:49)

• Winning on Housewives:
  • “Winning is...walking away from it...having the conviction to know, I believe in that, and next season, I’m gonna show you...And winning is also just allowing the audience to walk through that process with you.” (15:06)

5. Changing Landscape: Then vs. Now

• Old School vs. Influencer Era:
  • Dorinda and Lovett reflect on how earlier seasons were less curated, less strategic, and more authentic, compared to the polished, brand-focused approach of present day.

  “I think it was simpler times...You just went on and you were yourself, authentically yourself.” (09:36)

• Alcohol, Social Media, and Scrutiny:
  • They joke about “alcohol as the eighth Housewife” and agree that social media has made reality TV riskier and more stressful.

  “Now I would be very frightened to be on reality TV like that...Everything has changed.” (28:24)

• Social Media & Mistakes:
  • Dorinda admits she’s not constantly online and believes in simply owning up to slips:

    “For anyone to walk around like they’re so correct all the time is just fucking boring...We make mistakes all the time.” (57:04)

6. Female Friendships vs. Political Alliances

• Why Housewives, not House-husbands?
  • Lovett asks why the Real Housewives model doesn’t work for men. Dorinda explains the traditions of women gathering, confronting, reconciling, and the cultural bonds reflected in the show.

  “We like to gather in big groups...gossip and banter and tell each other off, then...love each other.” (25:40)

7. Political Advice—Bravo Style

• If politics were Housewives:
  • Jon poses a scenario: If Pete Buttigieg were joining "Real Housewives of DC" with Trump, Marjorie Taylor Greene, JD Vance, etc., how should he play it?

    “It’s either, you know, beat ‘em or join ‘em at that point...Or maybe...pretend like you’re joining them and then throw in the ax at the end.” (46:07)

  • Best Democratic Reality Star:
    • Dorinda picks Kamala Harris:

    “She’s a character...I wish we saw more of that, because she’s actually brilliantly smart...She has a quiet greatness about her that would create both mystery and fear.” (47:01)

8. Reflections on Political Past

• Dorinda’s Political Connections:
  • Dorinda reminisces about her late husband's deep involvement in Democratic politics and bipartisan think-tanks, mentioning Hillary Clinton and Madeleine Albright.
  • She laments the loss of bipartisan camaraderie and the polarization of modern politics:

    “Politics were a much different thing back then. They weren’t scary. It was something everybody could be involved in without getting stuck on one side or the other.” (51:05)

• Funny Political Anecdotes:
  • Stories involving famous figures like Nelson Mandela and Desmond Tutu stopping by her house.

    “One night, he had Nelson Mandela stop by the house...he just came from...the Regency...he brought him over for like 10 minutes. And I was like, wow, this is really a moment.” (52:16)

9. Ramona Singer: Political Aspirations?

• Instagram “Scandal”:
  • Dorinda discusses replying to an infamous Ramona post (with Daniel Penny), admits her accidental involvement, and stresses not everything should be overanalyzed online.

  “I thought she looked very pretty. I don’t know if there’s anything about the person next to him...It’s not that deep.” (56:14)

• Ramona for Office?:
  • Dorinda speculates on Ramona’s potential as a successful candidate:

    “I wouldn’t put it past her...She may win...Ramona...is brilliantly smart...She’s very switched on. Don’t let it fool you.” (58:50)

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Notable Quotes & Memorable Moments

• Dorinda on Housewives Dynamics:

  “I always say portraits can’t be participants. If you want to be a portrait, then stay on Instagram...But this is gonna...peel an onion. And the longer you’re on, the more the onion is peeled.” (15:06)

• On sudden fame:

  “I realized, uh-oh, the veil has been lifted. It’ll never be the same again.” (12:55)

• On Authenticity:

  “You can’t be dull and you can’t be inauthentic. And you can’t lie. ‘Cause if you lie, boy, one of us will figure it out. We’re the grim keepers when it comes to that.” (38:30)

• On Mistakes and Cancel Culture:

  “Just make it real simple. I made a mistake. Don’t try to get a...PR team. Just say, oh, I made a mistake.” (57:42)

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Timestamps for Key Segments

• Opening—Politics and Reality TV Introduction: 01:14–02:41
• Becoming a Housewife, Losing Control, and Public Grief: 03:04–12:55
• Strategy & Confessionals: 13:08–14:56
• Drinking, Social Media, and the Changing Reality Landscape: 27:24–29:54
• Political Parallels & Advice for Politicians: 36:16–47:22
• Personal Stories—Political Events & Famous Friends: 49:04–52:16
• Ramona Instagram Controversy & Possible Political Run: 55:28–60:03
• Closing Reflections: 60:11–61:38

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Tone & Style

Throughout, Dorinda is candid, self-deprecating, and witty—often teasing Lovett, reflecting deeply about her life, and pushing back on narrowly defined labels like “mean” or “villain.” The conversation stays light even as it delves into somber topics like grief and political disillusionment. Lovett’s humor and curiosity balance Dorinda’s warmth and matter-of-fact honesty, blending playful banter with meaningful commentary.

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For Listeners Who Missed the Episode

This episode offers an entertaining and insightful look at how the reality TV landscape offers lessons for understanding modern politics. With memorable stories, sharp analysis, and laugh-out-loud moments, it’s a must-listen for anyone fascinated by the intersection of pop culture, authenticity, and public life. Dorinda remains as beloved and unfiltered as ever, providing a unique perspective on both Bravo and America.

Transcript

[Jon Lovett]

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[Dorinda Medley]

I can't believe I'm agreeing with that, but okay.

[Jon Lovett]

I know it's not.

[Dorinda Medley]

That's gonna be the first time I hear it. Love it or leave it. It's Love it or leave it.

[Jon Lovett]

Hey, everybody, it's Jon Lovett. Welcome back to Love it or Leave it presents brilliant Bravo America. I'm sitting down with some of my favorite personalities from reality TV because I genuinely believe that you cannot understand politics in this moment if you don't understand the dynamics of reality television. Here's how Congresswoman Sarah McBride put it on Pod Save America earlier this year. Some of my colleagues are treating me the way they are treating me for a couple of reasons. One, it's because they want attention, right? They want to employ the strategies of a Bravo TV show to get attention in a body of 435 people. And the way to do that is to pick a fight with someone and throw wine in their face. Today is a big day for me because I am talking to the one and only Dorinda Medley, one of the icons from the Real Housewives of New York, the queen of making it nice. It was so much fun talking to Dorinda about everything, from how she sees her time on Roni, her thoughts on what Our elected officials can learn from the Housewives. And surprisingly, how she feels about her former castmate Ramona Singer today and Ramona's chances if she ever decided to run for office. Truly, it was such a blast. Such a, like, charismatic and interesting and vulnerable person, but also a really tough person, which is, I think, two of the qualities that made her such an amazing figure on reality television. So here she is, the one and only Dorinda Medley. I just want you to know, when we finish, everybody wants to gather for a photo.

[Dorinda Medley]

Oh, I'd love that.

[Jon Lovett]

God, here are the people that. That we've done that for that have been. People have been so excited about that. We've done the photos. Kamala Harris. Oh, Bernie Sanders.

[Dorinda Medley]

Okay.

[Jon Lovett]

Megan Rapinoe. Elizabeth Warren. Who else is on that list? Julia Louis Dreyfus. A lot of people don't. Bill Nye, the Science Guy. A lot of people don't make the list.

[Dorinda Medley]

Obviously, I'm doing something right outside of Housewives.

[Jon Lovett]

Dorinda.

[Dorinda Medley]

Yes.

[Jon Lovett]

Welcome.

[Dorinda Medley]

I'm very excited to be here.

[Jon Lovett]

So you and I have something in common.

[Dorinda Medley]

Okay.

[Jon Lovett]

Which is we have a shared experience, and it is this. We know what it is like to fly halfway across the world, film a reality competition show. Okay. Then spend six months having people say how excited they are to see how we do and not being able to say how we did.

[Dorinda Medley]

Yes. Very, very. I had to exercise a lot of discipline on that one. A lot. I would walk down the street and people would be like, oh, my God, I'm so excited for you to be on trainers. And I'd be like, well, don't get that excited. I mean, it was really hard.

[Jon Lovett]

I was on a plane, and Julia Louis Dreyfus was like, I'm so excited you're gonna be on Survivor, and I can't wait to see how you do. And I'm just thinking, ugh, she's gonna watch me go home first.

[Dorinda Medley]

Oh, I. I'm gonna tell you something. I was in such a state of. When I walked in. First of all, I'm thinking, I've got this. My daughter, who you know, is at Harvard getting her PhD, so she studied the whole thing. I had a 20 page how I've broken down the UK one verse. Read that. I was reading the Art of War. I was reading all these poets. I was working. I spent, like, $10,000 on trainers. The clothes, the clothes, the clothes, the looks, the looks. And I'm thinking, I am smarter. I am a warrior. And guess what happened? The piece of paper. You are murdered. I was beside myself.

[Jon Lovett]

It's unbelievable.

[Dorinda Medley]

It was fear and grief. It was a combination of fear and grief. And I think it was because I was like, how do I. Like, first of all, I got to go home. First of all, you can't even leave your apartment or be on social media or to literally go from being sequestered to being sequestered in your life. Yeah. Because you can't. You have to pretend like you're still there.

[Jon Lovett]

And I don't know if you had this feeling because. Because failure. Well, sure.

[Dorinda Medley]

Humiliation, absolutely. Fear, but also sadness.

[Jon Lovett]

Halfway around the world to get punched in the face. No one made you do it. You chose to do it.

[Dorinda Medley]

Well, I didn't think about it like that. I just was so deeply disappointed because it was the first time, and this was the great. I always say you walk away from everything with a. Learn, hopefully a lesson. Yeah. And it was the first time that I couldn't control it. You know, like on the Housewives, it's not that you can control it, but you could sort of very cleverly create your narrative and manipulate others. Like, this was the first time that it really was a game of chance. I couldn't even. I remember calling someone at NBC and saying, I'm so sorry that I disappointed you. He's like, you didn't. You weren't even long enough on long enough. They just. In fact, we think in the long run, it's going to be a compliment to you because they obviously were afraid of you at some level. And of course, I couldn't buy into that because I'm just thinking. But it actually worked out fine because I think I got as much press as the winners. In fact, I may have gotten more.

[Jon Lovett]

I'll tell you something, they got you out because you're a threat. That worked on me. That made me feel better about it, so. So you first pop up on Real Housewives in an earlier season as a friend.

[Dorinda Medley]

Couple times.

[Jon Lovett]

Couple times.

[Dorinda Medley]

Not even as a friend. Just as background.

[Jon Lovett]

Just as background. You're just in the background.

[Dorinda Medley]

Well, as their friends. Yeah. But not in a friend role.

[Jon Lovett]

Right, right. Not an official friend role. You just were on the show.

[Dorinda Medley]

Because we're all friends.

[Jon Lovett]

You're all friends. Is it true that you were offered, or at least you had entertained the idea of being on the show a few years before you were ultimately on it?

[Dorinda Medley]

Well, here's the thing. It was a very different. The way they handled it back then. Now I think it's gotten much more form and official. And back then, you know, we all just Knew each other. So, like, I remember it was Ramona's, like, they're doing a show, and we're all, like, hanging out somewhere. You know, just dropped her because her daughter went to school with my daughter. So it was like, they're doing a show, and they're gonna follow us, all of us around, and they're gonna. We're gonna. I'm thinking, well, why? Like, that's the most ridiculous. Why would they follow you around? Right, right. And at the time, Hannah was at a private school, and I wasn't with her father anymore, so he would have never considered it. And I just was at a different point in my life where, first of all, I really didn't understand the concept. And, B, I just wasn't in a position where I could. I wanted my daughter on TV so young. Right? I just thought. And so I just started Ramona, and all of them would be like, well, come to this. Come to that. So it always was like, are you gonna come on next year? Are you gonna come on next year? And. And, you know, after I married Richard, I couldn't do it either because he was involved in speechwriting for Hillary Clinton and the Council of Foreign Relations. So then I had to be that wife, you know, the political wife that was very up for east side and, you know, fancy and chic. And then after he passed, Ramon was like, okay, now it's time. And it wasn't very formal. I went and had lunch with one of the people, and they said, okay. And I did a film, and that's it. I got a contract. I was originally only going to do it one year and kind of try to be a friend of. But obviously that didn't work. I'll tell you one thing, but I remember I was in Ramona Singer's kitchen doing our first scene in the Hamptons. And I remember that camera coming around and thinking, oh, I like the camera, and I think the camera likes me.

[Jon Lovett]

So that's what.

[Dorinda Medley]

Yeah, this is great.

[Jon Lovett]

What. What you. Yeah, you had. You definitely clearly were. You found your calling. But what was your. Yeah, I think you might have. But what was your feeling?

[Dorinda Medley]

That's a positive and a negative, but let's go with.

[Jon Lovett]

Right. Well, I want. We'll get to that. But, like, what. What was your impression of reality TV before you were on it? Like, what did you think about it? Had you consumed it? Were you aware of it?

[Dorinda Medley]

Well, I watched it. Of course. We all. I mean, back then, reality TV was such a new concept. I mean, Bravo and all that kind of thing. They weren't really real channels to anyone yet. So you got to remember, I come from the era where Bravo. You're like, I hate to say it, and they're going to kill me, but it was kind of like a skip channel. You're like, oh, what is this Bravo?

[Jon Lovett]

Right.

[Dorinda Medley]

And then reality tv, kind of. This concept was so new even before the Housewives, when we had Queer Eye first straight guy. Wow. What is that? And so you started to engage at a different level, which was reality. And even I, as a viewer, started to fall in love with the character. So you really thought in a different. You know, you watch a movie, you don't really know these people. You know, they're acting, but all of a sudden you're like, I really like that guy. Top Felicia, I think we're gonna be friends. You know what I mean? There's definitely a crossover. So I was engaged in it. But, you know, I know it sounds ridiculous, but I think it was simpler times.

[Jon Lovett]

Yeah.

[Dorinda Medley]

You know, so I don't think there was a lot of thought process. You just went on and you were yourself, authentically yourself. And you gotta remember, all of us knew each other so well that. And they were all in it together. We both knew each other so well, but we also knew that, you know, we made a commitment, and we come from an era that if we sign our name to something or commit to a job, we do a great job. I think my generation is very competitive, very, like, has to succeed at everything they do and do your best and don't let anyone down. So you just went in there and you just were kind of your authentic self. And I don't. I think the real question is, wasn't what did I think of? It is, what did I think after the fact? That's the real question.

[Jon Lovett]

Well, that's what I. I was curious about that, so. And it does seem like there's multiple afters. So there's filming, right?

[Dorinda Medley]

Yes.

[Jon Lovett]

And there's what you feel about it after you've filmed it.

[Dorinda Medley]

Well, I didn't know. I was like. Because I had no idea. I didn't even know what editing meant. I kind of. In this weird way, even though we were filming 6, 10, 12 hours a day, I just thought it all went on there and they could see everything. And I'm sure I was just hoping for the best. And you know, and also, too, you have to remember, it was soon after that posting of Richard passing and Hannah going off to college. So I was sort of like a toothpick in the ocean. I was sort of like, didn't. I had lost all the titles that sort of. I kind of cherished, you know. And I was like, what am I doing now? And so for me, it was a great way to occupy myself. And it was also very therapeutic. Right. To be with all my girlfriends six days a week and have purpose again also, too. I think what I realized very. Am I talking too much?

[Jon Lovett]

No, you can't. There's no. We got a lot of time to fill between the mattress, so don't worry about that.

[Dorinda Medley]

I think what it was. For me, I think the biggest revelation was for so many years, you know, I'd been, you know, Hannah's mom, you know, Mrs. Lynch, you know, my first husband's wife, Mrs. Medley. Like, these were these. These, you know, kind of labels that I put on myself or jobs that I love. Listen, I love doing it. I would do it all over again. I have no shame. And that. And was very committed to that in all ways that it was really interesting to all of a sudden just be Dorinda. That's it. For the first time. People just were falling in love with Dorinda, you know. And I found that really interesting. And I really didn't take that on until I came out. And it was funny when it first came out. I'll never forget it. They had done. Back then, we used to have to be super secretive, so no one knew you were on. Now they post it as soon as they're doing their first scene. It's posted everywhere. And your big come out was you got a open page on the New York Post of spread. So that came out and I was like, oh, my God, I'm famous. Like, look at how glamorous I am. Right. Cause I've never seen myself in that way. Right. And I remember the next morning, I went to my favorite. I would walk, come out of my building. Across the street was this fruit guy that I'd do two things. I'd get a coffee and then get a piece of fruit and go upstairs. And I would just have on like a sweatshirt and my leggings or pajama bodies. And it was like seven in the morning. And this person turned to me and said, oh, my God, are you doing the medley? And I was like, yes. Now where have we met?

[Jon Lovett]

You know what I mean?

[Dorinda Medley]

And I realized, uh, oh, the veil has been lifted. It'll never be the same again.

[Jon Lovett]

And so. But so there feels like there's two experiences of watching it. One is seeing the edit and seeing yourself.

[Dorinda Medley]

Yeah.

[Jon Lovett]

And then the Other is seeing what you couldn't see, what people were saying. And I'm wondering if that affected how you thought about being on the show going forward.

[Dorinda Medley]

Like, I don't know if it affected me, but it was a learning curve, because you realize there's. There's a. There's an art. It is a bit of an art of war. Like, there's some people that are very clever at, like, just being one way when you're filming, and then they use the confessionals to destroy you. Right? So I'm like, oh, I can actually do that like that, you know, so you start to like anything. It's a learning curve. It's a strategy. It's a. And some people were brilliant at it. Like, Bethenny Frankel was brilliant at her confessionals, for sure. You know what I mean? There's nothing like a Beth Frankel confessional.

[Jon Lovett]

Well, that was. I mean, that seemed also jarring for the other women on the show, which is they would see the confessionals from Bethany be like, well, holy shit, she ripped me to pieces. So there's a quote that you have in your book about the show being chess in high heels that you have to march in like a military general, but at the same time, on the show, you're saying, this is me. This is who I am. And that doesn't feel like those can both be true.

[Dorinda Medley]

Of course they do. I mean, I think they're both true, because I think the difference is I think I march into all my life with heels on, with a sergeant judge. I mean, I'm barely ever playing checkers. I'm kind of in life always playing chess, you know, But I think it gets exacerbated a bit when you have the cameras on and you're filming 12 hours a day. So you really have to be prepared for what's. And it's coming, like it or not, you know, you have to be prepared. And after the first season, you have to decide if you have the mentality, the stamina, the wherewithal to take that on. But it's a shock, right? It's a shock, right?

[Jon Lovett]

It's like competitive friendship, like you said, you know, you're attacking perpetually and reevaluating your situation and how to win. What is winning?

[Dorinda Medley]

What is winning? Winning is probably twofold. It's walking around, walking away from it, even after the show airs. And even if you don't get the response from the audience, you like having the conviction to know. I believe in that. And next season, I'm gonna show you and I'm gonna build on this. It's a buildable thing. And winning is also just allowing the audience to walk through that process with you. Listen, I always find it very interesting that people go in this, especially now when they're so knowledgeable and stuff. You sign the dotted line, they're pretty clear about what you're doing. And if you don't want to take the good, the bad and the ugly, which is what being authentic is, and you just want it to be, you know, I always say portraits can't be participants. So if you want to be a portrait, then stay on Instagram, be an influencer, do a TikTok. But this is gonna, you know, it's like peeling an onion. And the longer you're on the show, the more the onion is peeled. And that ultimately is a good thing because you hand it over to the audience and they take from it all these things and they decide, I like this person. Yeah, microle. There's things I don't really enjoy about her, but I've done that before. But macrily, I get her and I will choose to engage in her and have a love affair with this charact. Hey, don't go anywhere. There's more of Love it or Leave It Coming up.

[Jon Lovett]

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[Dorinda Medley]

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[Jon Lovett]

Are there moments where you, you've talked about the show? Yeah, there are moments where you've been reflective. You said the show can make you protective and the show can make you reflective. Are there moments that from the earlier seasons where a similar moment could have happened later but you caught yourself that, oh, you're about to do that thing that you hated seeing yourself?

[Dorinda Medley]

You know, honestly, probably no. Probably. No, I don't. Because I don't. I think when you're in it and you're in the days are so long and you're so engaged that a, you forget about the cameras and baby, you just, you're who you are. And in a weird way the screw ups become the great memes, you know, and you reconciling them or bringing them around and having to go through the process of trying, attempting to make both your colleagues and your audience to understand it is kind of where the rub is, but also where the growth happens.

[Jon Lovett]

Yeah, there's. Well, part of it is knowing yourself, but you have to trust yourself. But you also have to trust the show a little bit.

[Dorinda Medley]

Yes, of course, the whole thing. You know, you gotta remember this show. Yeah, you have these incredible characters, but there's layers and layers of people. Your cameramen, your sound people, your editors, your production company, Bravo NBC. And I will say that throughout the years when I was on, they're in constant communication with you and they do carry you through the process. So, you know, you're sort of dealing with your production company first, which is shed and smaller. They do their thing, then they give it to Bravo. So then Bravo kind of takes you over and does through the pr. Then it goes to NBC, which is sort of like the big daddy, right? At that point, you're either cooked or you're whatever, right? So you have to lean into it. But you never feel like, even when you're going through it, you never feel. I could only speak from my own experience, but I never feel it. I never felt abandoned. I felt like, oops. Well, that probably wasn't such a great season. Hopefully I'll do better next year. You know what I mean? Or, oh, my God, that's a great season. But there always was something that came out of it that I think. I always say, and I still think it applies today. When someone new comes on at the end of the season, you should be able to take six things from them. What are the six things you learned about this character that is gonna create a love affair? It's like when you first go on dates. Oh, I really like his family, or I like the fact that he does this, or his hobbies. And I think if you can do, like, for me, I was. I had Bluestone Manor. I lost my husband. I was friends with these girls. I like to make it nice. I love holidays. You know, just all these kind of things that people are like. I'm a great. I think of myself as a good mother. I'm ballsy. I tell it like it is. You don't want to pull shit on me, you know? Cause I'm going to call you out every time, right? So all of a sudden, there's people that are like, okay, I can get my hands around this girl, and I want to see how she's going to grow on the show.

[Jon Lovett]

That's so fun. That's so interesting, because I understand how that would be your list of six. But when I think of you on the show, to me, it's two things. It is one that you're incredibly vulnerable, that you're actually. And that you are open. You know, you go on this trip with Carol, you're clearly on this show at a period of transition, a difficult period of transition in your life, and people forget that.

[Dorinda Medley]

You gotta remember, I was only, like, two years out. I don't even know if it was from, you know, going through that, but that was. What a beautiful gift that was, not only for me, but for a lot of People that, you know, were young. I always, you know, I think about that time and, you know, people would call me a widow, and I'm like, I'm too young to be a widow. So I was misplaced there, too. You think about a widow as some old. I remember this woman at Elios one night was talking to me. She goes, so are you here with your husband? I said, oh, no, I'm a widow. She goes, oh, no, you're not a widow. I'm a widow. I'm 18. You're something else. Just unfortunate, but not a widow. Very Upper east side. I was like, well, thanks a lot. It doesn't really make it better, but, you know, I think to have someone to discuss that with, and then the amount of people that reached out and, like, really just, like, found peace in it and didn't feel alone. Because, as we know, there's certain things. Divorce can be one of them. Death can be another things. You can feel isolated and not shameful, but you don't know how to connect. And it was a great way to connect on a level that you could share this kind of thing that was going through. It was a teaching moment as far as I'm concerned.

[Jon Lovett]

You know, I would write a lot of jokes for. You know, I wrote jokes for politicians. And what we would find is the more. The more honest you are about your own flaws, joking about yourself, the harder you can be on somebody else.

[Dorinda Medley]

I don't know if that's true.

[Jon Lovett]

Well, here's what I mean by it. I mean that. What, it gives you the space to go harder on other people whilst people still like, you're one of the meanest people that I love. Right. You are.

[Dorinda Medley]

You think I'm mean?

[Jon Lovett]

Oh, there are moments. There are moments in this show where you are.

[Dorinda Medley]

I disagree with you. No, I'm honest. Yeah, I'm honest. And I may call it out, but I don't know if I'd call it mean. And usually, if you notice and you go back, it's always in response.

[Jon Lovett]

Yeah, absolutely.

[Dorinda Medley]

To something I always say in life. I'll never shake your hand first, but I'll shake it back hard.

[Jon Lovett]

Well, absolutely. No, not saying it hasn't come back.

[Dorinda Medley]

So that's not mean. That's like, we gotta put a stop to this.

[Jon Lovett]

Let's say tough.

[Dorinda Medley]

Tough. That's a better word.

[Jon Lovett]

Extremely tough. Extremely tough.

[Dorinda Medley]

Cause mean's labeling.

[Jon Lovett]

Yeah, well, I. Harsh. There are moments of.

[Dorinda Medley]

And probably well deserved.

[Jon Lovett]

And well, well. And never for abs. No one's saying otherwise. No one saying otherwise. Well, There's a line you said, and.

[Dorinda Medley]

I think that's the. And you're doing a little housewife for you, because that's the way to. To corner you or put you in a box. It's not because you can't ever micromanage a situation. You gotta look at the macro and understand, do I shut the shit down and I do that in my own life. It just happened a couple days ago. I was like, now we're done. I've been lenient, I've been good. But that's a very Sagittarian trait. You know, when you're good, you're great. When you're bad, you're terrible. You know, I will be a sleeping tiger, but you pull my tail one time, I'll let it go. Well, you pat me on the back, I'm great. You start to touch my mouth, well, then you're gonna get a bite, aren't you?

[Jon Lovett]

I mean, honestly, people like it. People like. But yeah. Well, you said. There's one point. You said, treatment like a dog. I'll bark.

[Dorinda Medley]

Yeah.

[Jon Lovett]

So the reason I bring that up is there's no show like Real Housewives with men. It just doesn't exist. And I wonder why you think that is. Like, what is it about women in a show like this that I think there's good and bad. So I think part of it is just like it's conceivable for a men to be interesting.

[Dorinda Medley]

I've thought about that. Cause you're absolutely right. I've thought about that. I don't know if it's just historically, we tend to gather together. Like, I come from a very Italian Polish family, but mainly Italian because my mom's Italian. So of course you always lean to or. In our family, it was. Everything was Italian Italian. And whenever there was a room of aunties and uncles and grandmas and cousins and all the women in the kitchen, it was an. You know, Christmas morning would start off great, but by two, someone was fighting. You know what I mean? They were this and you did that. And then at the end of the night, they all kissed each other goodbye and off they went. And I think there's something about women that are together and these were just very. You don't see. I don't. Anyway, you know, men just gathering. We love to gather. We like. I mean, listen, I always say all you gotta do to sell something on Instagram is say girls Weekend. They'll stampede to it. Like, we just love Girls Weekend. So girls retreat and everybody. That's who we are, we like to gather in big groups and just, you know, gossip and banter and tell each other off, then get back together and then love each other. There always ends with a cry. We love a good cry, you know, at the end of the week. And so I think it's just historically how we kind of roll and then that obviously gets, you know, it gets shown on tv and you gotta remember some of those days we're filming, they're long. You may see it in an eight minute clip, but that may be hours. And sometimes you start at 8:30 in the morning. On those girls trips, you don't go to bed till midnight.

[Jon Lovett]

Yeah, it seems exhausting. I was watching it, but it's fun. It, it. Well, you kept going back for more. You're still going back for more.

[Dorinda Medley]

Well, no, I'm not. I don't know. What show are you talking about? I'm not on?

[Jon Lovett]

Well, you've been on. You've been. Well, all right, yeah, fair enough, fair enough.

[Dorinda Medley]

Let the record show. Did I miss something? Didn't miss anything.

[Jon Lovett]

Didn't miss anything. But it also sometimes feels like alcohol is like the eighth housewife on the.

[Dorinda Medley]

Trip, of course, and that like shows up. Alcohol is the 8th is A. This is what I love is when people start to question things when. What party have you been to? A bachelorette party. Have you been to a bachelor party?

[Jon Lovett]

That's the party I've been to.

[Dorinda Medley]

Have you been to a bachelor party? Are they usually sober? Have you been to any picnic where it's usually sobered? Have you been to a wedding? Alcohol is usually involved in most of our life. So I don't think you. I think it's very easy to corner it to these things because. But of course, I mean that's just a given and I think they've lessened that. You know, we had free reign, you know, like I said, it was a bit for me anyway and I'm just speaking, I have to use all those words like allegedly. I mean, I've covered myself now. Right, Allegedly, Allegedly, allegedly. You know, it was much more of, I think the Wild west because we didn't worry so much about everything. Now I would be very frightened to be on reality TV like that because, God, we've gone through so much, you know, in the last five or six years. Everything has changed. The rules and the regulations, what you say, what you don't do. It's very monitored that I actually think it'd be much harder to be on reality TV full time now because you can get in big trouble.

[Jon Lovett]

You Think because of the reaction, because of the people paying attention.

[Dorinda Medley]

Yeah. I just think the stakes are much higher now. I never thought about it is. That sounds so weird. I never thought about it. I never worried about it. Of course I was like, ugh, that was a bad episode. But I didn't really walk around with also too. I think the social media game is so intense now. And the, and a lot of the bloggers and stuff, like they're really running. They're really running the. They know more than we know. So it was a much more of like we'd be filming and it was a big mystery until it came out and there wasn't that voracious studying and, and, and just micromanaging everything and pulling out every word and talking about this and lawsuits and like it's scary now. Yeah.

[Jon Lovett]

That's so. There's something about like I know that.

[Dorinda Medley]

I never once walked away from the show thinking I'm gonna get sued or I said something wrong that's gonna get me in big trouble.

[Jon Lovett]

Yeah. I mean, I know that when I've had nights. Cause I agree. You know, alcohol is part of my best and worst nights.

[Dorinda Medley]

Of course. For all of us. And you'd be silly and ridiculous not to admit that.

[Jon Lovett]

Right. Of course.

[Dorinda Medley]

You know, we're only human and that's part of the authentic people. And that's one thing that you can call out in reality is when you know someone's playing one game on the show and then the minute they. The cameras are off, they're doing it all and you're like, wait a second.

[Jon Lovett]

That must drive you crazy.

[Dorinda Medley]

Of course. And then that bleeds into whatever else because you're like, what? So there's a lot of stuff you have to take in.

[Jon Lovett]

Yeah. One time I drank too much and called on Joe Biden to withdraw.

[Dorinda Medley]

I was thinking about even the Love Hotel that was on now. And when that. Who's the host names again? Joel. Whatever. Yeah. You know that when I was reading those Instagrams, I'm like, oh, someone was drinking too much because he must have. I just thought to myself, because we've all done that Instagram or that late night. I mean I. I remember once I texted something late night and I woke up next morning, I was praying at 6:30 that I didn't write it. I'm like, it was a dream. It was a dream. I was like, oh my God.

[Jon Lovett]

Well, yeah, well, you have those moments. That's the thing that I. What I was feeling when I. Whenever I see. Which is you have those Moments in life where you've. And by the way, sometimes it's just a truth you weren't ready to share yet. Or maybe you don't always say it in the most articulate way, but it's heart's coming out. But it's very different when it's also gonna be on television in a few months. Or is it not?

[Dorinda Medley]

Who cares?

[Jon Lovett]

Who cares? Who cares?

[Dorinda Medley]

Who cares? So Sally in Iowa doesn't like me for a couple weeks. I'll win her back. Well, you know what I mean. All right.

[Jon Lovett]

And you do win her back.

[Dorinda Medley]

And it doesn't change my life. I get up and I do the same things and everything's the same and. And I never really was. I think also, too, that's different now is it's a much more branded thing. Like, everybody was selling something or branding something or really curating their image. I mean, half the time you saw me and we were in our bed, we didn't even brush our hair. Like, we just wasn't that curated. Well, I remember I wouldn't even have the wardrobe or the makeup people. I'm not gonna say who. But I was in NBC about, I don't know, a year ago, and I was doing something for Bravo Insider or something, and in walked one of the housewives that was a new housewife. And they had a whole team with them. I never. I still. I just have Ryan here, and that's like. I never had a team. I never had people. Like, it was just, I. If we were gonna do a press tour, I would be like, luanne, you wanna share a car? You know? And then there were crazy conversations, like, what? I was laughing with Ramona the other day. I said, remember this time? And literally, we didn't. There was no room to complain or say, we're not doing it. There's a lot of that now, too. Like, we just got our schedules and we were like, o. I remember when we gathered at NBC, this is a true story. And we were laughing about it the other day, and they said, okay. You know, Bethany and Carol, they're going to Good Morning America. We're like, oh, that's not fair. Okay, whatever. What's my assignment? Okay? And then they do Luanne and Sonia. You're going to something else. You're going to H and M to be in the jumbo trial. I'm like, well, that's a good one, too. Why didn't I get that one right? So it's left with Ramona. So Ramona's like, well, okay, what are we doing? They said, oh, you're going down to Times Square, and we're going to stick you on the Jumbotron. And you're going to say. One of you is going to say, and the premiere of Real Housewives in New York City. And the other person is going to bite into a hot dog in front of a hot dog stand. This is true. You probably can still pull it up. And Roman was like, well, I mean, I don't eat hot dogs, so, like, I'll do that. And you're going to. I'm like, well, okay, I'll eat a hot dog. But I. They're like, we won't put a lot of ketchup on it so it won't spill on your thing. I'm like, oh, well, you could put ketchup on it.

[Jon Lovett]

So, of course.

[Dorinda Medley]

And I'm thinking, that's how that went down. They drove us down. I'm like, okay, tell me when to bite. Into the hospital we go in the Jumbotron. Everyone goes, and tonight, the premiere of Real housewives, a Dear CC's or whatever. And I go, right. And that was it. No discussion, no rehearsal. Check. We're next.

[Jon Lovett]

You know, you're just like a team player. You're just into it.

[Dorinda Medley]

Well, we all were.

[Jon Lovett]

Yeah.

[Dorinda Medley]

And we all were excited for press days. There was really no team, no nothing. Ramona was always worried about where we're gonna have lunch, you know? You know, it was just sort of like another day to be all together.

[Jon Lovett]

Yeah. Also, those trips seem so grueling, but it seems like for Ramona, it was, like, just a vacation.

[Dorinda Medley]

Oh, Ramona thought they were real vacation. She would call me up and be like, oh, my God, are you back for the holiday? I'm like, like, what holiday? Like, no, no. She really, really. But Ramona was remarkable because by the time we got to these, I'm thinking about it, like, okay, we were filming. By the time we got to any place, Ramona would have every restaurant, every restaurant owner, every nightclub, every contact that she, like, owned. Owned it. Like, she's remarkable like that. And there wasn't a time that we would stop filming that she then wouldn't go out.

[Jon Lovett]

It's. So that's.

[Dorinda Medley]

Well, I was like, oh, my God, it's 11:30. We've been filming since day. I'm gonna go out. I was talking to Joe, and he's very excited about us coming. So I'm like, all right. So that's what people don't realize. When the cameras went off, we were still sort of all together. I think there was one time when you. Bethany, I think or someone released the tapes of us after the cameras went off and it was Halloween and we were on the pool table and people were like, now, why. Why aren't we part of that? Because we really did stay awake with each other. All we were. You know what it was like? I think it's because we come from that college era where we all hung out in sororities and stuff. For us, it was like we were back on spring break again and we were making money.

[Jon Lovett]

You know what I mean?

[Dorinda Medley]

And being loved, generally.

[Jon Lovett]

Generally, it seemed like we were just ourselves. Like, it seemed like it would bug you when, say, like, it's the morning, you've all just woken up and, like, Tinsley walks in, full glam, and you're like, how are you already so made up?

[Dorinda Medley]

Well, Tinsey went to sleep with full glam. Like, I think she just would. Like, she would keep her eyelashes on and everything. Tinsey was always perfect.

[Jon Lovett]

Yeah, well, the.

[Dorinda Medley]

That's her era, but I think that's. But she would. She would go to sleep with her eyelashes and stuff. And she was much more. Even in her. When you see her filming, she was always very well put together. We were put together well. But, you know, we had. We. It wasn't a huge concern. Like, if we weren't cast partying, that stuff. You kind of came into our lives and saw what we really.

[Jon Lovett]

Right. Well, it just seems like you were less concerned, which is what made it good tv.

[Dorinda Medley]

We weren't concerned.

[Jon Lovett]

Well, because it was. There's. I think that, like, one way in which what's happened in reality TV has sort of come over to politics is. And Trump says this kind of thing all the time, which is, it's great to be loved. It's fine to be hated. The only thing you can't be is boring.

[Dorinda Medley]

I agree.

[Jon Lovett]

And, you know, we talked.

[Dorinda Medley]

I can't believe I'm agreeing with that, but. Okay. I know that's gonna be the first time.

[Jon Lovett]

Hopefully he was the last. But the. We Talked to Sarah McBride, who is a congressperson from Delaware, and she said, some of my colleagues are treating me the way they treat me because they want attention. They want to employ the strategies of Bravo TV to get attention in a body of 435 people. And the way to do that is to pick a fight with someone and throw wine in their face.

[Dorinda Medley]

She might be correct. With the current day we live in, she just might be correct. And we're seeing it happen over and over again. And sadly, I don't like it. But there is effectiveness in that.

[Jon Lovett]

Yeah. Like that must be something you feel when you watch politics now.

[Dorinda Medley]

A hundred percent, you feel like deja.

[Jon Lovett]

Vu, like, oh, wow, that's a move I saw Ramona pull.

[Dorinda Medley]

Yeah. And I think, you know, I think all things in life are kind of political. Marriages can be political. Reality TV can be political. I mean, there's a lot of things in life where people can apply strategy. And I don't think this is any different. Right. Yeah. And for us to think that politics, I mean, I think if anything, in the current age we're living like it or not. And you know, whatever your opinion is, you do what you want. But it is a learning curve that it wasn't all that. It seems like it is a lot of movement and jiggering and game playing and stuff. Or at least that's been my experience watching it because maybe because I grew up in an era where the six o' clock news was your only knowledge. And now you see that there's a lot of other stuff that goes on that is unfortunately or fortunately very reality tv. Like.

[Jon Lovett]

Well, because part of it's about attention. Yeah, it's about getting attention. And Trump figured that out. People like Marjorie Taylor Greene have figured that out. So.

[Dorinda Medley]

And, and you can't take your eyes off it for good or for bad. You're like, what? You know, so reaction is reaction.

[Jon Lovett]

Yeah.

[Dorinda Medley]

No one survives on reality TV if they're dull.

[Jon Lovett]

Right.

[Dorinda Medley]

Well, and also dull is the kiss of death.

[Jon Lovett]

And the other part of it too. And I think about watching no two.

[Dorinda Medley]

Things not to interrupt you. You can't be dull and you can't be inauthentic. And you can't lie. Cause if you lie, boy, one of us will figure it out. Well, that's. We're the grim keepers when it comes to that. Hey, don't go anywhere. There's more of Love it or Leave it coming up.

[Jon Lovett]

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[Dorinda Medley]

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[Jon Lovett]

Just thinking about the people that have come and gone. Some have been dull, but some of the people are trying to put on a show. That's right, they're trying to. They have an idea of who they want to be on the show. And it's interesting. Both in reality TV and modern politics, that doesn't fly like the truth will.

[Dorinda Medley]

Out, even if it takes a while. Yeah, you know I always someone said to me a while ago, well she's her first season's great. She's going to be a great reality star. I said, oh, the first season's nothing. That is just when you're slowly every. You know, you're vetted to be the new one. And there's a mad love affair that happens. The second season is where the tire hits the tar because that's when they either produce and start peeling that onion or the audience starts to get bored of it, because the imperfections will be as interesting to the audience as the perfections.

[Jon Lovett]

Well, also.

[Dorinda Medley]

And that's the difficult part. That's the rub.

[Jon Lovett]

And you've already. There's, I think I imagine going through watching yourself, seeing the talking heads, seeing the online reaction, seeing the edit and then doing it again and not trying to kind of be risk averse. Must be very difficult.

[Dorinda Medley]

Not trying to be risk averse or, you know, being.

[Jon Lovett]

Willing to do what you want.

[Dorinda Medley]

You know what's so interesting about this? You're overthinking how much we thought about it.

[Jon Lovett]

Okay, that's.

[Dorinda Medley]

That's the problem. Why? It's difficult to answer this because you're applying things that we just. We would literally end filming and go back to our normal lives and not really think about it until they were like, you start press next week. And then you went through that. Then we would put our work hats on again and go through the process and mourn it, be horrified, be happy, be thrilled. I say, it's like, what would I. It's like belonging to the NFL. Okay? You get on the field, you beat each other to the pulp. You put do great passes, you do bad passes, you're frustrated, you're happy, you're high fiving, you're like, what the f? And then you get off. And that night you're having dinner, patting each other and saying, high five. Spring trainings in six months, so let's have some fun until spring training. It's a little bit like that. And I think that's what makes a great reality star. You have to be able to be strong enough to. Well, I think the relationships have to be strong enough to cycle through it and understand what you're doing, because if you don't, it'll kill you internally. And you see that happening to people, they just can't not take it on. And they eat it, they drink it, they sleep. I remember Hannah said to me one day after I'd finished filming, and we were at work door shopping, and someone said, oh, my God, it's Dorinda. She goes, no, we're not doing that Dorinda medley thing from the Housewives, right? We're back to Normal again for a couple months. Right. You promised me, Mom. And I was like, yes, I am. Yeah, because I don't want to do that now. You promised. It doesn't start again until September. I said, okay. So we would. Were very good. And that's an art form in itself, to transition back and be able to wake up the next morning and be like, well, I guess there's not a car service waiting for me. And back to reality. I got to go wash my dishes and unload the dishwasher. Like, you know what I mean?

[Jon Lovett]

Yeah, well, I bet. I bet you may not have overthought it. I overthink everything. For the record, but I mentioned people that have struggled on these shows have been.

[Dorinda Medley]

Have been doing some overthinking. And also, too, that stakes are much higher now. I mean, we're seeing people go to jail. We're seeing people do this. All these things that I, you know. But again, I go back to this. It's not that I don't have empathy or sympathy. It's that you kind of sign the contract. So I remember someone said to me right before I started Housewives, one of the final things that they said, now, remember, if you're gonna do this all, do you have any skeletons in your closet? Because all your skeletons will come out eventually, so you gotta be prepared for that. And I remember thinking about that, thinking, what would be the most embarrassing thing that could come out about me? And I was like, I think I'm good. I will own up to all of them. And I pay my taxes. So I think we're gonna be okay.

[Jon Lovett]

You know, you gotta pay your taxes.

[Dorinda Medley]

And I haven't been in a sex scandal or I've never sent a dirty video. So I think we're okay. Okay.

[Jon Lovett]

So if, let's say, Pete Buttigieg or another Democratic candidate told you he's about to shoot the real Housewives of D.C. and he's gonna be joining the cast with Donald Trump and Marjorie Taylor Greene and J.D. vance and Marco Rubio. And you're trying to advise this person. You're their kind of confidant. They're about to go into battle in high heels. Not Pete in high heels. But, you know, what's your. How would you. If you were thinking about politics as a reality show, what would be your advice for how to kind of go into taping and win?

[Dorinda Medley]

That one's tough, because that would be a tough one, because you'd have to. I think someone like him would have to rethink his whole strategy. I mean, that is a sink or swim. That is a swim. It's either, you know, beat him or join him at that point, depending if you want to. That's the problem.

[Jon Lovett]

That's the problem.

[Dorinda Medley]

If you want to stay on tv, I think you're gonna have to. Or maybe I would say probably pretend like you're joining them and then throw in the ax at the end. Collect information, create an environment where they get very comfortable with you and they're exposing too much, but at the same time, be the skull collector. And then at the end in the reunion, just like, slam that shit.

[Jon Lovett]

We need an insider. We need somebody to get inside. You know, I went back and.

[Dorinda Medley]

But that would be. Yeah, he probably wouldn't make a second season because, well, what would we do? And probably, to be honest with you, J.D. vance and those people would be great reality stars. I'd watch it.

[Jon Lovett]

Well, that's the problem. That's the problem. Well, who's a. Who do you see out there that would be a good, democratic reality star? Who's the person that's built for this moment to you that you think, oh, wow, that's a person who'd be a great housewife? See, this is the problem.

[Dorinda Medley]

Kamala Harris.

[Jon Lovett]

Kamala Harris. Kamala Harris. That's a good one. That she could do it.

[Dorinda Medley]

I think she's a character, and I think she's fun. And I wish we saw more. One more of that, because she's actually brilliantly smart. Number one, she was a prosecutor for years, so you can imagine the skills that she has. I mean, you need those good prosecution skills when you're executing it through housewives. And she has a quiet greatness about her that would create both mystery and fear.

[Jon Lovett]

Do you think that she has at times made a mistake that housewives have made about trying to.

[Dorinda Medley]

Oh, my God, you're gonna get me in trouble.

[Jon Lovett]

Etiquette.

[Dorinda Medley]

Oh, gosh.

[Jon Lovett]

The.

[Dorinda Medley]

Yeah, exactly. That's how it all begins.

[Jon Lovett]

That's how it all begins. But no, but that, like, there's a. That maybe she was a little bit held back, a little bit afraid to be her full self, and people sense.

[Dorinda Medley]

The woman had no time.

[Jon Lovett]

Right.

[Dorinda Medley]

I mean, that was just. I just thought the whole thing was, you know, she just had no time. I. I. What. What did we have? Six months? You know what I mean?

[Jon Lovett]

Last three months. Three months.

[Dorinda Medley]

I mean, I think considering the time she had, that was very difficult thing to do. Even coming into it, probably getting that call, she was like, oh, my God. There wasn't a lot of preparation for that. And let's face it, those people are usually groomed for what, two or three years beforehand. So that alone was a feat to watch.

[Jon Lovett]

You know, I went back and looked and.

[Dorinda Medley]

And I don't want to be political, but, you know.

[Jon Lovett]

Yeah, I went back. Or do I dude be political? I went back and looked and I found. Because I was Hillary Clinton's speechwriter.

[Dorinda Medley]

Oh, my God. So was my husband with. With Madeline Albright in those early days.

[Jon Lovett]

Those are years before me.

[Dorinda Medley]

Yeah, yeah, of course. Well, I know that he would be 72 now. I'm not saying you're the.

[Jon Lovett]

But I went back.

[Dorinda Medley]

That's impressive.

[Jon Lovett]

I honest, I was very overwhelmed, and I was not qualified.

[Dorinda Medley]

That's a hard job.

[Jon Lovett]

It was a really hard job. And I developed a kind of twitch in my nose for a while because I was 23. 20. I was 23, 22 when I got the job.

[Dorinda Medley]

Oh, my God.

[Jon Lovett]

I was completely in over my head. But I went back and pulled her old calendars, and there it was in 2006, fundraiser Hillary Clinton, Richard and Dorinda Medley.

[Dorinda Medley]

Yes.

[Jon Lovett]

And so you did a fundraiser at my townhouse. At your townhouse? Yeah, on the Upper east side.

[Dorinda Medley]

Well, they were very close, and so was when Madeleine Albright was very good friends. You know, but even that's so interesting is that back then, when Richard was involved with the DNSA and the council formulation and all the Richard Haass and all them. All of McConnelly's rights, it was much more of a bipartisan thing. Although you were loyal to your parties and worked very hard for your parties. And like, you'd go to the council formulations and the bipartisan thing is really. Was such an incredible think tank. There wasn't that, you know, sort of. Yo, you're either a Republican or Democrat now. They were much more open about speaking and learning from each other than it is now. I kind of miss that. Right.

[Jon Lovett]

No, it is. Well, you feel that in the show, right. Because there was something about 2016. Oh, my God.

[Dorinda Medley]

I can't believe you found that in the calendar. Dennis. Dennis. What's his name? Yeah, Dennis Chang raised that.

[Jon Lovett]

Of course.

[Dorinda Medley]

Isn't that so weird that we remember these things?

[Jon Lovett]

Absolutely. But you're right that politics feels more fraught in part, I think, because.

[Dorinda Medley]

So separated.

[Jon Lovett]

It's separated. But also because Republicans have got. Become the Trump. Republicans have become so extreme that it starts to intrude on Real Housewives.

[Dorinda Medley]

Well, it starts to intrude about creativity because people, you either are one or the other. And part of Those kind of bipartisan think tanks, like the council or whatever, was an ability to. I remember Richard used to have big, huge talks with Trump Jr. And not Trump, Bush Jr. And he'd come over and he just found them, even though he was one party. And Richard was that. They just learned so much from each other. Especially during. Remember, I come through the time when they were dealing with Saddam Hussein and they were dealing with bin Laden. There would literally be think tanks in my garden with all of them, Colonel Powell, all of them, and then these wacky characters that I wasn't, you know, which would be like, why don't you not come down? Because so and so is coming. They were the wacky characters. You know them.

[Jon Lovett]

Yeah.

[Dorinda Medley]

They don't look like they're anything, but you certainly don't want to wrong them. And I remember one of them I was in the kitchen with once, he said to me, you know, the best thing about coming here is having a piece of lasagna. I was like, well, are you going to kill me now? You know, because they were like that. You know, they were personality, listen. But crucial to this sort of, you know. And then that's when you would have all the great thinkers, people that, I don't know, you would even think of now, and they would literally openly talk about. I think about it now as like a person that was just like, oh, my God, I gotta go grocery shopping, because they're having a think tank thing in the garden today. I'm gonna make something really nice. You know what I mean? But when I think about that now, in retrospect, in the learning curve for me, and especially when I talk to Hannah or even Richard's kids, it's very embroidered in who they are. Because politics were a much different thing back then. They weren't scary. It was something everybody could be involved in without getting stuck on one side or the other. Right?

[Jon Lovett]

Yeah. Yeah. I mean, I know. So the other day.

[Dorinda Medley]

God, that's wild that you found that calendar there.

[Jon Lovett]

It was.

[Dorinda Medley]

Yeah.

[Jon Lovett]

I was like, oh, my God, I might have.

[Dorinda Medley]

And you know who was at that was Desmond Tutu.

[Jon Lovett]

Wow.

[Dorinda Medley]

Which is amazing. And then I remember when they had. One night, he had Nelson Mandela stop by the house, and I was literally in the living room, and he just came from. I think they were at the Regency, because he used to stay at the Regency. Right. And where all the politicians stayed. And he brought him over for, like, 10 minutes. And I was like, wow, this is really a moment. Because she goes, in that world, as big as it is, it's very tiny back then because they had their clubs, you know what I mean? Their clubs of men that they would move around in. I think I have a picture of it somewhere. I should find it. I kind of forgot about all that stuff. That was another life I had to let go.

[Jon Lovett]

You think Nelson Mandela saw Luann at the bar at the Regency? I mean, what are they doing?

[Dorinda Medley]

I do remember being in an elevator with Netanyahu and all the security guards and thinking, that guy's kind of cute. Who is he? Richard's like, come on now, Jordan. I really did. I didn't know who he was. That is a true story. They were closing the thing. I'm like, richard, we can fit in. So we get in and it was Netanyahu. And he smiled at me and he said, hello, are you. I really didn't know who he was. I know I'm probably gonna get a lot of shit about that. But remember, it was like 20 years ago and I was much younger and more interested in fashion than politics. Hey, don't go anywhere. There's more of Love it or Leave it coming up.

[Jon Lovett]

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[Jon Lovett]

So speaking of politics, so Ramona post this picture of her with Daniel Penny and you replied beneath it, oh, Ramona, you look great.

[Dorinda Medley]

And then you Yes, I did. And I stand by that.

[Jon Lovett]

Well, she had. But then like everybody was like, holy shit. Why, why is Ramona posting this? Why is Ramona? No.

[Dorinda Medley]

People were wondering why I responded because I said she looks pretty. To tell you the truth, Again, I am a number one and Ryan can agree to this and everyone. I don't, I don't know again, if it's just not my interest or I'm so I'm not a person that's always on Instagram. I just, just don't do it. So I go to my main people, Luann, you look great. Or Ramona, I miss you. So I didn't really. She's always with these Palm beach characters. I didn't really know who it was. I know that's gonna sound terrible.

[Jon Lovett]

No, no, it's.

[Dorinda Medley]

And I responded, ramoni looked pretty and I stand by it. I thought she looked very pretty. I don't know if there's anything about the person next to him. Well, the reason people, when they ask me about it and I'm a person that when you ask me about something, I answer you, yeah, because if I didn't, if I, if I did it, I'll tell you why I did it. Even if it's a mistake. I was. So someone called me, said, or wrote to me, you know, right away, some people call from those numbers. They said, did you write this? I said, well, clearly I did. It's on, it's on the Instagram. What are you asking me? I don't understand the questions. Katie said, well, why did you say that? I said, because I thought she looked pretty. It's not that deep.

[Jon Lovett]

It's not that deep.

[Dorinda Medley]

Yeah, but like, can I put that in print? I said, well, it's already in print on Instagram. Just take a screenshot of it and I'll put it on my own Instagram. I mean, I just don't. That's what I mean about social media. Everything now. And that's a bad thing. Everything now is torn apart, is like, picked apart and overanalyzed. And I think ultimately, not just for this, but for a lot of things for this generation. It really does take away from your ability to be creative and be free and maybe make mistakes. You know, we. For anyone to walk around, like, they're so correct all the time is just fucking boring. We're not. I make mistakes all the time. Ask Hannah Lynch. I mean, Hannah. Hannah thinks I'm a walking. You know, Hannah's like, I'm so surprised at this point in your life, you haven't been canceled or something because you do things that, like, you know, how.

[Jon Lovett]

Could this be canceled? You can't be canceled.

[Dorinda Medley]

Uncanny. No, but she's like, mom, it's not 1960 anymore, you know, so we make mistakes. And I think the best thing about making mistakes, it's just make it real simple. I made a mistake. Don't try to get a. Don't hire a PR team. Don't try to, like, hide away from it. Just say, oh, I made a mistake.

[Jon Lovett]

Well, it does seem like. It seems like part of your. Gives you that power. Right. Is that you know who you are. You're not afraid of who you are. And so people. And people already know you. So if you do say, you know what, I screwed up, people take that at face value.

[Dorinda Medley]

Yeah, Just like, I didn't know. Thanks for telling me. It won't happen again. You know, And I always say. I used to say on housewives, if you're really in bed, so someone would come to me and be like, I don't really know how to get. I mean, it's like, just cry. It works. It works with men. It'll work on housewives. Just a good tear.

[Jon Lovett]

Get pulled over. Get pulled over, cry. What do you like? There's rumors that Ramona is going to run for office. No, there's not that. There's that she's doing these photos. She's flirting a little bit with the Maga stuff that's in Palm Beach. That's what I. That's what these are the rumors.

[Dorinda Medley]

I wouldn't put it past her. And you know what? She may win. That's the.

[Jon Lovett]

No. I'd be scared to run against her. That's for sure.

[Dorinda Medley]

Literally. Ramona. What? People don't know about Ramona. Or maybe they do. She's brilliantly smart. And I consider myself a smart person. I can't say that about all the housewives, but she's very smart. She's very switched on. She's good. She's good. I go to, like, I consider myself very switched on financially. And we're always talking about post tag dollars and what are this? And are you going to put an llc? Like, we're. We're really. I do because I have money head, so. But Ramona will lay. Ramona will lay it out for you. The best thing to do. Don't do an llc. And if you'll be like, okay, that's great. That's great. Hold on. Let. Call my accountant if you need my accountant. She's very. Don't let it fool you. You know, don't let it fool you that she's this wacky person. There's nothing wacky about Ro.

[Jon Lovett]

You can see that. You can see that.

[Dorinda Medley]

And listen, she was part of an era where she was doing Running D. Now, people probably don't even know this, but she was part of the first part of these discounters like Whack Daffy and TJ Maxx and Marshalls and all these things that were just starting. And she. She sweeped up in the garment district. She was connected to everyone. And I worked in the garment district at the time for Liz Claiborne. I knew who she was. Cause we would outsource all the stuff to her.

[Jon Lovett]

Wow. Last thing before we let you go. You didn't know what this show was?

[Dorinda Medley]

No, I knew.

[Jon Lovett]

You had no idea.

[Dorinda Medley]

But it's better like that.

[Jon Lovett]

But this is okay, right?

[Dorinda Medley]

It's beautiful conversation. I'm good at this kind of stuff. I could be with you all day long. We're playing verbal comeback. To me, this is like a date. I want to go over and kiss you. I would take you home. This is the kind of date I like.

[Jon Lovett]

Honestly, if I hadn't just gotten engaged. I just got.

[Dorinda Medley]

There you go.

[Jon Lovett]

And also, you're not my type. Gender wise. Gender wise. Gender wise. Stunning, stunning woman.

[Dorinda Medley]

But I'm glad you cleaned it up there at the end.

[Jon Lovett]

Got to clean it up. Got to keep it nice. Got to keep it nice. Well, Dorinda Medley, this has been so much fun. Everyone here is Such a fan. Oh, great. I do think that, like, we have.

[Dorinda Medley]

Yeah. Thank you. It was really fun. I enjoyed it and I learned a lot about myself. No, I'm not getting it.

[Jon Lovett]

Well, no, I do think that there's something about. There's no one who has, I think, a better perspective on how politics has become like reality TV than someone who has gone to battle and won and done both. Yeah. You lived in both worlds.

[Dorinda Medley]

In both worlds. Yes. Yes, yes. It's so. Thank you for bringing up that thing. It just took me down memory lane because in order to survive through all this stuff, I sort of place that time with Richard, you know what I mean? He makes me want to cry a little bit. So I appreciate you bringing that up. Well, there is that very sentimental to me. Cause I was that person, you know?

[Jon Lovett]

Well, you're still that person, aren't you?

[Dorinda Medley]

Yeah, no, of course. But I think for survival's sake, you know, you have to sometimes compartmentize in order to. But when you brought it up, I was like, God, I actually remember what I served at that dinner. It like, took me back. So sorry about that, guys.

[Jon Lovett]

But I think this is why people love you, because there is this person right there. You're so tired. You know, I got within 3 inches of facing the tiger and I said.

[Dorinda Medley]

Well, I'm going to back and you're back on my lap with me petting you.

[Jon Lovett]

There you go.

[Dorinda Medley]

That's the art form right there, ladies. You want a husband, you want anything. You're not kidding.

[Jon Lovett]

You throw into medley, everybody. If you're already scrolling endlessly, which we know you are, don't forget to follow us at Crooked media on Instagram, TikTok and all the other ones for original content, community events and more. You can also find the Love it or leave it on YouTube for videos of your favorite segments and other YouTube exclusive content. And if you want to type our praises or rip us a new one, consider dropping us a review. Finally, you can join Crooked's Friends of the Pod subscription community for ad free Love it or Leave it and POD Save America episodes subscriber exclusive pods and more. Sign [e-mail] friends love it or Leave it is a Crooked Media production. It is written and produced by me, John Lovett and Lee Eisenberg. Kendra James is our executive producer. Bill McGrath and Ken Caroline Reston are our producers. And Kennedy Hill is our associate producer. Hallie Kiefer is our head writer. Sarah Lazarus, Jocelyn Kaufman, Peter Miller, Alan Pierre and Subha Agrawal are our writers. Jordan Kantor is our Editor Kyle Seglin and Charlotte Landis provide audio support. Stephen Colon is our audio engineer. Our theme song is written and performed by Cher. Sure. Thanks to our designer Sammy Cadearna Rhys for creating and running all of our visuals, which you can't see because this is a podcast. And thanks to our digital producers David Toles, Claudia Shang, Mia Kelman, Delon Villanueva and Rachel Gajevsky for filming and editing video each week. Our Head of Production is Matt de Groat and our production staff is proudly unionized with the Writers Guild of America East.

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[Jon Lovett]

Inspires I won't let my moderate to severe plaque psoriasis symptoms define me emerge.

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[Dorinda Medley]

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