Let’s Be Honest with Kristin Cavallari
Podcast: Dear Media
Episode: The Hills: Old Habits Die Hard (Season 5, Episode 14)
Air Date: January 6, 2026

Episode Overview

In this episode, Kristin Cavallari rings in 2026 and returns to her popular "Hills" rewatch series. She breaks down Season 5, Episode 14, “Old Habits Die Hard,” sharing unfiltered insights and behind-the-scenes secrets from her time on the show. Kristin discusses her real relationships vs. their onscreen portrayals, the constructed drama between characters, and how certain storylines—like those about family and addiction—played out both in reality and on camera. The tone is candid, confessional, and often humorous, as Kristin sets the record straight on the “Hills” experience and reflects on how she’s changed since her reality TV days.

Key Discussion Points & Insights

1. The “Hills” Lunch with Lo & Production Oddities

• [02:00] Kristin voices surprise at how her season 5 relationship with Lo was portrayed with no context for their suddenly friendly status:
  • “Lo and I have hung out a few times, but, like, Lo was talking shit on me, and then she’s just at lunch with me all the time. I think it’s kind of bizarre they didn’t really bridge that gap or address it at all.”
• Kristin emphasizes that, despite the show’s attempt to inject drama, her real friendship with Lo was steady, with their only true issue coming in a later “Birkin incident.”

2. Awkwardness of Family Filming & Stepmom Dynamics

• [05:00] Kristin admits she had “zero recollection” of filming the scene at her dad’s house, highlighting her uneasy, “unstable” relationship with him:
  • “I never really liked filming with him, if I’m being completely honest. And so that’s why I thought I would maybe remember this... my dad always sort of put on a show as a typical narcissist does.”
• She describes shock at her stepmom Nicole appearing on camera, given their history and Nicole’s long-standing “hate for MTV.”

Notable Quote:
“She had just gotten a nose job... put on a jean skirt and Uggs... She was me for Halloween. That just—I'm just telling you this to paint the picture for you.” (On her stepmom, ca. [08:30])

3. The Justin Bobby Storyline: Fact vs. Fiction

• [13:30] Kristin dissects her storyline with Justin Bobby. She asserts the ‘love triangle’ was “bullshit” and produced for the show:
  • “We knew when to be there. We had call times. Again, I never stayed at this house unless we were filming.”
• Kristin shares that, in real life, she’d never allow a guy to “break my heart” repeatedly or stand her up:
  • “If someone is messing with me or not treating me the way that I needed to be treated, I have never had an issue with closing the door, walking away, telling someone to kick rocks.”
• She recognizes the producers’ use of proven formulas (love triangles, friend drama, victim narratives).

4. Engineering of Scenes & “MTV Lines”

• [17:10] Kristin calls out specific dialogue as obviously scripted:
  • “If that’s not an MTV line, I don’t know what is.” (On her dad asking if she’s seen Stephen or Lauren)
  • Points out the projection in her dad’s comments about Brody, observing, “Brody was never full of himself... what my dad was saying about Brody was such a projection. It’s not even funny.”

5. The Real Story Behind Holly’s Drinking & Recovery

• [27:00] Kristin investigates the authenticity of the “Holly’s drinking” storyline by texting Heidi Montag directly:
  • Heidi confirms it was real, and that Holly has been sober since 2011 and now runs a women's recovery center.
  • “Shout out to Holly... she’s out there helping a ton of other people. And I just think it’s really incredible.”
• The “intervention” scene with Holly, Heidi, and Spencer was not staged, and marked the beginning of Holly’s sobriety journey.

6. Behind-the-Scenes of Iconic Filming Locales

• [35:00] Kristin reminisces about the Spanish Kitchen (site of Holly's intervention), sharing a personal anecdote about calling off her own engagement and then doing a wedding dress photoshoot the next day:
  • “What does my dumb ass do?... I went to the photo shoot and... afterward, I met one of my really good friends, Pip, at Spanish Kitchen, and we took so many shots of tequila.”

7. Justin Bobby & Kristin: Manufactured Romance

• [44:30] Kristin pulls back the curtain on the supposed intimacy between her and Justin Bobby:
  • “They make it seem like he is spending the night and we’re probably gonna go do the damn thing. Which, guys, never again. Never happened. Never spent the night with Justin Bobby.”
• She notes sarcastic exchanges (“Are you having fun?” / “I’m having the time of my life”) as examples of the artificiality.

8. Music’s Role in Shaping “The Hills”

• [54:30] Kristin credits the show’s music supervision for manipulating audience emotion and “telling you how to feel” in key scenes.

9. Brody Jenner & Bentley the French Bulldog

• [56:00] Kristin details her real-life relationship with Brody:
  • “Brody got it. Brody was always a team player.”
  • Reveals Brody bought her Bentley (“I just had no business having a dog at 18!”).

10. The Explosive Final Scene: Justin & Audrina at the Thompson Hotel

• [01:00:00] Kristin observes real emotion and subtext between Justin and Audrina:
  • “To me, this scene felt very heavy in a lot of ways, and, like, there was still some wounds.”
  • Quotes Justin:
    • “A big part of me will always have feelings for her and... I would never be able to say anything was better than Audrina Patridge ever in my life.”
  • Kristin reacts: “It’s kind of sweet, and also, I’m watching it like you’re a scumbag.”

Notable Quote:
“I think Audrina, it was probably harder for her because she really did like Justin, you know, she really is going on dates with Derek, I think, trying to move on from Justin because she’s upset that I’m... in her mind, dating him.” ([01:03:10])

11. Production Choices & Kristin’s Retrospective Wisdom

• [01:08:30] Kristin reflects on “missed opportunities” for real onscreen friendships (especially with Heidi), and the artificial division of cast roles by production.
• She closes with genuine anticipation to see how the old scripted drama continues to play out:
  • “I can’t wait to see how he breaks my heart. You know what? The other thing I will say is, to me, what would have made the most sense was to have me filming with Heidi... But instead it’s Stacy the bartender and it’s Lo, which is fine, you know... but Heidi and I had real history together.”

Memorable Quotes & Moments

• “I always had a pretty un—I was gonna say unstable relationship with my dad, a pretty weird relationship with my dad. I was always very uncomfortable around him.” ([06:15])
• “We knew when to be there. We had call times. Again, I never stayed at this house unless we were filming.” (On Justin Bobby "showing up", [45:00])
• “If someone is messing with me or not treating me the way that I needed to be treated, I have never had an issue with closing the door, walking away, telling someone to kick rocks.” ([14:10])
• “Brody got it. Brody was always a team player. Brody brought his A Game.” ([56:15])
• “A big part of him will always have feelings for her and that he would never be able to say anything was better than Audrina Patridge ever in my life.” (Kristin quoting Justin, [01:00:30])
• “Fuck, man, it is. It's a good show. I'm sucked in. I'm knee deep in the drama and I'm dying to see what happens.” ([01:06:45])

Episode Structure & Timestamps

• 00:00-03:00 — Opening remarks, New Year reflections, episode’s focus
• 03:00-09:00 — Analysis of Kristin & Lo’s friendship depiction, filming at her dad’s house, stepmom stories
• 09:00-15:00 — Discussing Laguna visits, constructed drama with Lo, Brody/Jade’s toxic relationship
• 15:00-19:00 — Justin storyline: “completely bullshit”, formulaic MTV devices
• 19:00-24:00 — Onscreen awkwardness with dad, “MTV lines,” Brody projection, boundaries Kristin struggled with
• 27:00-36:00 — Holly’s drinking storyline, real-life sobriety, praise for Holly’s recovery work
• 36:00-38:00 — Spanish Kitchen anecdote, botched engagement, “living in the moment”
• 44:00-47:00 — The Malibu house dinner with Justin: “never spent the night with Justin Bobby”
• 54:00-55:00 — Role of music in shaping the viewing experience
• 56:00-59:00 — Brody Jenner, history, Bentley the dog
• 01:00:00-01:06:00 — The final Justin/Audrina scene, authenticity, love triangle fallout
• 01:08:00 — Reflections on production, real vs. forced friendships, expectations for next episode

Final Thoughts & Takeaways

Kristin delivers trademark honesty and insight, deconstructing the difference between what viewers saw and what actually happened during “The Hills.” She highlights production tricks, owns past insecurities, and celebrates both the messy drama and real growth of cast members like Holly. For fans and new listeners alike, this episode is a fun, candid, and occasionally emotional ride through early reality TV history—with enough “WTF” revelations to make even the most seasoned viewers re-watch with new eyes.