Podcast Summary: "Are You A Charlotte?"
Episode: Inside The Playboy Mansion with Holly Madison
Host: Kristin Davis
Guest: Holly Madison
Release Date: February 13, 2026
Overview of the Episode
In this intimate episode, Kristin Davis welcomes Holly Madison—former Playboy Mansion resident, television personality (notably from Girls Next Door), and bestselling author—for a candid discussion about the surreal intersection between Sex and the City and Playboy culture. The conversation explores the filming of the iconic LA episode at the Playboy Mansion, the reality versus fantasy of life there, evolving attitudes toward female sexuality, and the complexities of empowerment, exploitation, and pop culture myth-making.
Key Discussion Points & Insights
1. The Surreal Experience of Filming at the Playboy Mansion
- Kristin Davis, who played Charlotte, describes the Mansion as “very surreal, very strange” and reflects on internal conflict regarding glamorizing Playboy for television.
- Holly Madison reveals she hadn’t moved in yet when the episode filmed but was a dedicated viewer of both Sex and the City and Girls Next Door:
- “I’m so bummed I missed out... I just missed Sex and the City, which is such a bummer because I’m such a big fan.” (03:21)
2. Playboy’s Mainstream Moment & Party Culture
- Holly discusses how Playboy parties in the early 2000s were “the cool parties in LA,” hard to get into and bucket-list events for many:
- “It’s hard to believe, but those were like the cool parties in LA that you wanted to go to... When I got invited to my first one, I was so excited.” (04:45)
- Details on how guests were invited and which events were the biggest (Midsummer Night’s Dream, Fourth of July, etc.).
- Behind the scenes, parties were both intimate ("less than 50 people") and at times sprawling, depending on the event.
- “Fun in the sun pool parties... were pretty intimate” but “the 4th of July party... went from day to night; that’s kind of the one that most resembled what you did on the show.” (06:07)
3. Daily Life at the Mansion vs. Public Perception
- Routine described as oddly structured and monitored, with set curfews, weekly club outings, restaurant nights, and movie viewings:
- “We had like a famous nine o’clock curfew. And then there would be different activities every night...” (07:26)
- Contrasts the quiet, almost office-like daytime ambiance with wild party nights.
4. The Reality & Struggle of Being a Girlfriend
- Holly shares that initially, Hef had “seven girlfriends,” leading to a competitive and inhospitable atmosphere:
- “That was just a nightmare. Nobody got along. It was a constant revolving door... all really competitive.” (09:15)
- Later years were calmer, with just three main girlfriends featured on Girls Next Door.
5. Weird Details, Haunted Vibes & the Sex Room
- Both recall uncomfortable aspects of the Mansion’s interior:
- Kristin: “We were scared... it had a carpeted mattress floor and mirrored walls... if you turned on a light, the mirror would disappear and it would be like sex statues...” (11:00)
- Ongoing rumors of the house being haunted and the “energy” feeling dark.
- “A lot of people thought that house was haunted, too.” (11:35)
6. Party Behavior, Gender Dynamics & Safety
- Kristen’s trepidation about portraying Mansion parties as purely fun or liberating.
- Holly explains party-goers "behaved" around Hef because “everybody wanted to stay on the list... more on their best behavior in front of him”:
- “I always say at the parties, I never saw anything too wild... people would be more on their best behavior in front of him...” (12:19)
7. Public Narratives vs. Personal Experience
- Both reflect on the messaging about female empowerment tied to Playboy—contrasting the 1990s/early 2000s mainstream embrace with shifting cultural perspectives.
- Kristin: “I felt at the time, you know, it was very much held up as being empowering for women in some way. But I feel like we don’t think of it that way now. That way, correct.” (20:56)
- Holly: “That was what I bought into as well... but I was just in the deepest, deepest, like, inner ring where it really wasn’t liberating anymore.” (20:56)
- Both express complicated feelings about whether the show contributed to glamorizing a myth.
- “I do feel just some mixed feelings about the fact that our show…was supposed to be empowering… but later on…maybe I was wrong.” (31:13)
8. Sexuality, Consent, and Cultural Messaging
- Candid discussion about the ambiguity and lack of transparency for women entering the world of Playboy.
- Holly: “People think you should have known what you were getting into…but there’s nothing like a contract…it’s something you get into little by little and kind of lose yourself.” (22:28)
- Both women reflect on how sex positivity for women often omits emotional nuance or the realities of power dynamics:
- “Women should just be able to have sex like a man and not care, and that’s empowerment…but nobody talks about the emotional impact of sex.” (39:15)
9. Impact on Future Generations
- As mothers of daughters, both wrestle with how to guide the next generation through sexual empowerment, consent, and societal expectations:
- “My daughter…still have sex ed classes that are about, like, consent and really important interesting things…But it’s so, so hard to navigate, 100 percent.” (40:55)
- “I think the more discussion, the better, honestly.” (40:59)
10. Holly’s Perspective on the Show and Her Role
- Holly affirms that the Sex and the City episode’s portrayal of the Mansion was accurate from an outsider’s perspective and didn’t trigger negative feelings.
- “Because it more captures the era where I still, like, only knew Playboy from the outside and was kind of fascinated by it.” (42:29)
- Pop culture accuracy: Holly praises the show’s costuming and set design for its authenticity.
- “The casting was so spot-on…some of [the extras] were Playmates, some of them weren’t…but the actor you talk to... looks like one of Hef’s buddies.” (24:01)
Notable Quotes & Memorable Moments
-
On the party invite mystique:
“When I got invited to my first [Playboy] party, I was so excited. It was just such like a bucket list thing.”
– Holly Madison (05:11) -
On the reality of being a girlfriend:
“It was just a mess…nobody got along. It was a constant revolving door.”
– Holly Madison (09:15) -
On the Mansion’s strange vibe:
“It definitely had a lot of, like, kind of dark energy, I would say. I mean, it’s kind of a dark house as well.”
– Kristin Davis (11:39) -
On consent and ambiguity in the Mansion:
“People are picturing that scene in Fifty Shades of Grey…there’s nothing like that up there. It’s something you can get into little by little and kind of lose yourself.”
– Holly Madison (22:28) -
On empowerment and regret:
“I’ve heard people…grew up watching Girls Next Door and thought it was so fun, so they thought the next best thing to get into would be porn. And now they regret it. So it’s crazy the effect those things can have.”
– Holly Madison (32:32) -
On the evolution of empowerment:
“It’s so hard to know when it crosses the line into not being empowering. It’s a very interesting, interesting thing, I think.”
– Kristin Davis (38:15) -
On the importance of open discussion for young women:
“The more discussion, the better, honestly…when I was young…the way it was portrayed…was like, women should just be able to have sex like a man and not care…and I feel like nobody talks about the emotional impact of sex.”
– Holly Madison (39:15 & 40:59) -
On which character Holly identifies with now:
“Back in the day…for sure a Charlotte…But as time goes on, I think I’m more of a Carrie. I’ve written a couple memoirs, so I identify as a writer. And all the anxious, attachment style, cringe stuff that Carrie does has totally been me.”
– Holly Madison (44:20)
Timestamps for Important Segments
- 02:27: Kristin welcomes Holly Madison and sets up the Playboy Mansion episode discussion
- 04:43: The mainstreaming of Playboy parties and how Holly first attended
- 07:26: Holly describes daily life and curfews at the Mansion
- 10:42: Description of the infamous "game room" and the Mansion’s peculiar decor
- 12:19: Discussion of what actually happened at parties and how people behaved around Hef
- 20:56: Kristin and Holly reflect on the changing attitudes towards Playboy and empowerment
- 22:28: Holly explains the ambiguous, “slippery slope” reality of being a girlfriend in the Mansion
- 31:13: Mixed feelings about contributing to glamorizing Playboy via Sex and the City
- 39:15: Deep dive into how pop culture has represented female sexuality and emotional impacts
- 44:20: Holly identifies as more of a “Carrie” than “Charlotte” these days
Tone & Takeaways
The episode is marked by honesty, nostalgia, and mature reflection. Both Kristin and Holly approach these personal, sometimes dark realities with warmth, humor, and mutual respect. They acknowledge the complicated legacies of both Sex and the City and Playboy, and the enduring importance of frank conversations about sexuality, agency, and media portrayal.
For Listeners New to the Episode
- This conversation goes far beyond behind-the-scenes gossip, instead offering a nuanced look at cultural change, personal evolution, and the ways in which media and lived realities collide.
- Holly Madison’s candor about her time at the Mansion—and the long-term emotional fallout—gives rare insight into a glamorized world, while Kristin Davis’s openness about her mixed feelings will resonate with anyone struggling to reconcile ideals with reality.
- The episode is filled with fascinating, sometimes surprising details about Hollywood, the nature of empowerment, and what it means to reflect authentically on the past.