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.

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)

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)

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

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.

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.