Let’s Be Honest with Kristin Cavallari

Episode: "Do I Want to Makeout With This Person?"
Guest: Justin Anderson
Release Date: October 21, 2025
Host: Kristin Cavallari

Overview

In this candid, laughter-filled episode, Kristin Cavallari sits down with her best friend and longtime confidant, Justin Anderson, for a wide-ranging (and often hilarious) deep dive into her current dating life, returning to the "Laguna Beach" reunion, and the challenges of finding real connection post-divorce. The pair get honest about attraction, what they want in relationships, and how age, location, and emotional intelligence factor into dating. Listeners are treated to their unfiltered banter, lots of playful teasing, and moments of real introspection as Kristin reveals her hope, excitement, and nerves about new romantic chapters.

Key Discussion Points & Insights

Reunion Vibes & Personal Growth

• Kristin talks about attending the "Laguna Beach" reunion and the cathartic experience it provided, despite her initial reluctance:
  • “I didn’t want to do it. And I’m really, really happy that I did… it was healing in a lot of ways, very therapeutic.” (00:23 – 01:20, Kristin)
• Justin expresses how the passage of time has deepened their friendship and allowed them both to "gel," making them the kind of friends who could actually live together but still maintain independence. (03:57 – 04:36)

Real Estate, Home Life, and Friendship

• The pair riff on Kristin's house, landscaping costs, and living arrangements, with Justin joking he’d love to buy land next to Kristin just to "be around you at all times." (03:25 – 04:29, Justin)
  • Playful banter about moving in, “It would just be my absolute dream to, like, live in your butthole, basically.” (03:25, Justin, teasing)
• Their rapport demonstrates the depth and comfort of their friendship, emphasizing understanding personal boundaries and compatibility.

Dating Intentions & Listening to Intuition

• Kristin opens up about intentionally taking a long break from dating to focus on herself, her kids, and her podcast tour.
• The duo discuss manifesting romance—Kristin describes literally asking the universe for a date, and almost magically getting set up with a high-profile coach through her agent soon after. (05:43 – 07:10)
• Physical chemistry is crucial: Kristin says her litmus test is, "Do I want to make out with this person?" She emphasizes that, while conversation and learning from people are important, the desire for physical connection is rare and non-negotiable for her. (09:30 – 10:04)
  • “It’s so rare that I want to have sex with someone.” (09:48, Kristin)

The Realities of Dating Apps

• Kristin explains why she deleted Raya, the celebrity dating app, citing lack of real connection and the abundance of narcissistic behaviors, especially among the “best looking guys” who don’t ask questions or engage in meaningful conversation. (16:29 – 20:17)
  • “Not one thing. Such a red flag for me with dating with men is like… you actually have to have a little back and forth and ask a couple questions.” (19:39 – 20:10, Kristin)
• She details the mechanics of properly deleting a Raya account and how misunderstandings about app activity lead to celebrity rumors.

Shifting Preferences & Age Ranges

• Kristin sets her age preference on dating apps higher—to 50—and finds more appealing options:
  • "A lot of the guys in that 45 to 50 range were actually better looking than, like, the 40 to 45 range." (17:46 – 17:55, Kristin)
  • Justin agrees that this slightly older demographic is typically more established and fits Kristin's “weathered real man” type. (18:03 – 18:12)

A Real-Life Romantic Plot Twist

• Kristin shares the story about meeting ‘Billy’ at an Oasis concert in LA—a serendipitous in-person encounter with a man she’d originally met in 2008 at Coachella (but completely forgot!). This time, they reconnect, exchange numbers, and spark a deep emotional connection quickly. (24:12 – 26:40 / 36:28 – 37:15)
  • “He had my number in his phone… from like, literally 2008. How crazy is that?” (36:57, Kristin)
  • They discuss the 'red string theory'—the belief that certain soul connections are destined to return, regardless of time and distance. (37:28 – 38:39)

Reluctance About Long-Distance and Children

• Kristin is realistic about the practical challenges of new romance:
  • Billy lives in LA, wants kids (which she definitely doesn’t), and has a life rooted on the West Coast.
  • She’s honest about not wanting the responsibility of changing someone’s mind about kids. (38:39 – 39:14, 41:30 – 42:03)
• They reflect on the ideal partnership at this life stage: two stable people with established careers, flexibility, emotional intelligence, and no urge to “change” each other.

The Emotional Labor of Dating

• Justin addresses the reality that guys can get very attached to Kristin quickly, and that she feels genuine empathy when things don’t work out:
  • “It really eats at you… And I’m the one who’s constantly saying… just say you’re not into it, you know, but you’re like, I can’t. I feel really bad.” (40:54 – 41:13, Justin)
• They agree breakup conversations are hard but necessary.

Online vs. Organic Connections

• Kristin asserts she’s manifesting meeting someone organically, "in the wild," outside of dating apps.
  • She notes a positive shift, seeing more "hot guys in Tennessee" after changing her mindset to abundance. (22:34 – 23:14)

Open-Mindedness & Moving Beyond Stereotypes

• Kristin is set up on a date with a man who previously DMed her on Raya; her friend vouches for his quality, reminding her to be open even to those who don’t seem “her type” at first glance. (44:26 – 47:00)
• She dislikes the “clean cut” stereotype and gravitates towards those who challenge and stimulate her.

Dating at This Stage of Life

• Both agree that, post-divorce and with clarity about her needs, Kristin can (and should) take her time, date multiple people, and hold out for magic:
  • “Sorry. F*cking sue me. I’ve waited this long. It’s gonna be pure magic.” (54:08, Kristin)
• They discuss the luxury and importance of independence and self-knowledge; Kristin values not having to "check in" and appreciates this phase of her life.

Notable Quotes & Memorable Moments

• On manifestation:
  “I said to the universe, I’m ready to go on a date. And the next day, I got a phone call from my agent.” (06:43, Kristin)

• On attraction:
  “For me, it’s really, like, do I want to make out with this person?” (09:46, Kristin)

• On connection vs. appearance:
  “If I saw them on a dating app, I would not have liked them like that… Personality can make someone really attractive.” (10:32, Kristin)

• On dating app pitfalls:
  “Not one thing. Such a red flag… If you’re on f*cking Raya… you have to have a little back and forth and ask a couple questions.” (20:03, Kristin)

• On fate and timing:
  “The red string theory… that invisible string that keeps you together… maybe you meet early and it doesn’t work out, and you come back…” (37:28, Kristin)

• On boundaries and independence:
  “I don’t have to answer to anyone. I don’t have to, like, check in at night… I’m so happy I don’t have that right now.” (48:43, Kristin)

• On dating and age:
  “Just because I went out with someone twice doesn’t mean I’m in a relationship with them. Like, that’s the point of dating… you can go out with multiple people until you are like, I actually want to be in a relationship with someone.” (52:53, Kristin)

Important Timestamps

• 00:23 – 01:20 — Kristin on the cathartic "Laguna Beach" reunion
• 03:25 — Justin: "Live in your butthole" joke about being neighbors
• 05:43 – 07:10 — Kristin manifesting a date, first outing post-break
• 09:30 & 09:46 — "Do I want to make out with this person?" discussion
• 16:29 – 20:17 — Raya deletion mechanics & narcissists on dating apps
• 17:46 – 18:12 — Preference for older men ("weathered, real man" banter)
• 24:12 – 28:16 — "Billy" Oasis concert story & phone call reconnection
• 36:28 – 38:39 — The surprise of Billy’s old number & 'red string theory'
• 38:39 – 42:03 — “Kid talk” realities and being honest about intentions
• 44:26 – 47:00 — Set-up by friend with a Raya DM-er, opening up to new types
• 48:43 — Kristin on valuing independence as a single mom
• 52:53 – 54:08 — The reality of dating multiple people and holding out for magic

Tone & Structure

• The episode is warm, open, and peppered with Kristin and Justin’s signature playful, sometimes sassy humor.
• There is plenty of affectionate ribbing, childhood nostalgia, and honest admissions about the high and low points of modern dating in your 30s and 40s.
• Kristin’s blend of thoughtfulness, self-awareness, and vulnerability will resonate with any listener—single, dating, or just self-reflecting.

Conclusion

A must-listen for anyone navigating post-divorce dating, this episode is refreshingly honest, at times self-deprecating, and ultimately empowering—reminding us that attraction is both mysterious and non-negotiable, magic is possible at any age, and the right partner will only enhance, never diminish, our sense of self. Kristin’s push to manifest a real, in-person love—while refusing to settle for less than “pure magic”—sets the tone for an exciting new chapter. Listeners are left rooting for her, wanting to hear how her Friday date goes, and feeling a little braver about their own dating adventures.