Modern Wisdom #1060 – Rick Glassman – The Case Against Condoms & Fake Friendship

Host: Chris Williamson
Guest: Rick Glassman
Date: February 16, 2026

Episode Overview

This episode features comedian and actor Rick Glassman, exploring themes of authenticity, boundaries in relationships and friendships, neurotic rituals, the role of vulnerability, and what it means to be truly "comfortable" with others. In a signature Modern Wisdom style, Chris Williamson and Rick weave humor, introspection, and personal stories across topics from literal and figurative “condoms” in relationships to the science and social dance of connecting with other humans—whether on stage, on a date, or even in shared spaces with their unique quirks.

Key Topics & Discussion Breakdown

Opening Vibes and the Language of Comfort [00:00–03:00]

• Cozy Clothing as Social Performance
  The conversation opens with playful banter about “cozy” attire and the tension between dressing for comfort vs. appearance.
  • Rick: "I like to wear things I could sleep in. If you show up someplace wearing something, people feel offended. Let me just find some really cool clothes that I could trick you into thinking is, 'Oh, look at—I could wear this to the big dance—but I could also go home and sleep in it.'" [00:24]
  • Chris: "Mine leans a little bit too sports-wear-y… if you're going out for a dinner in a Lululemon T-shirt…" [00:45]

The ‘Condom’ Analogy: Intimacy, Comfort & Honesty [03:00–05:16]

• Sexual & Friendship Boundaries
  Rick dives into his sensory sensitivities and likens using condoms during sex to not being truly present—extending that metaphor to emotional safety in friendships.
  • Rick: "When you make love or even have sex with a condom, it’s like, I'm having sex with contacts in. So I'm just aware they're there… And that's why I've learned… to never have physically intimate with somebody you don't feel safe explaining to them, 'Hey, I'm not present with you right now.’ I feel that way in friendships as well." [02:35]
  • Chris: "What’s the equivalent in a friendship?" [03:38]
  • Rick: "I guess in friendships, be able to have friendships where you don’t have to wear a condom." [05:16]

Boundaries, Sensitivities, and the Art of ‘Calling the Game’ [05:17–11:02]

• Navigating Personal Boundaries
  A deep dive into sensitivity (hear: OCD traits, codependency, overthinking), Rick describes learning to ask for and honor boundaries—his own and others'.
  • Rick: "The sensitivity is about my comfort… For a very long time, whatever I was thinking or feeling… I just assumed this is what you're thinking and feeling." [06:39]
  • Chris: "So you look forward to boundaries being set in that way. You’re a pro boundary person on the other side." [08:17]
  • Rick: "Yeah… And it wasn't until I was an adult that I realized not everybody likes to say that a lot. Some people will just, 'Hey, could I have…' They didn't want me to take their stuff and they gave me these toys and stuff. And I was like, 'Why wouldn't you tell me no?’” [09:50]

The Social Dance—Authenticity vs. Convention [10:25–14:15]

• Not Playing the Social ‘Game’
  Chris likens social interaction to tennis, discussing discomfort with directness. Rick advocates for stepping out of unspoken conventions to clarify intention.
  • Chris: "Sometimes going, 'Is this happening because of a you preference?...' feels a little sort of discordant…" [10:25]
  • Rick: "I'm just trying to better understand what game we're playing." [10:38]

Vulnerability, Small Talk, Behind-the-Bit [11:18–17:13]

• Admitting Feelings & Fears
  Rick shares his discomfort with small talk and fears around being liked, describing his desire for directness—such as asking someone after a date whether a kiss was genuine.
  • Rick: "My big fear is, what if I go in to kiss somebody and they kiss me back because it’s easier?" [11:54]
  • Chris: "Procedural kiss." [12:25]
  • Rick: "I take things at face value until I realized that I can't. So I'm just skeptical all the time." [12:26]

Self-Awareness & Growth: The Journey from Oblivious to Introspective [16:33–19:18]

• Evolving through Self-Awareness
  Rick recounts becoming self-aware, embracing correction, and choosing friends who are honest and direct.
  • Rick: "I was so much happier thinking everybody loved me than when I realized I'm bothering people. But now… I probably going to annoy people and just… there's only so much that is in my control." [17:13]

Information vs. Criticism: The Booger-in-the-Nose Rule [21:22–23:21]

• Valuing Feedback
  Rick compares being told you have a booger to seeking friends who will give honest, actionable information, not just criticism.
  • Rick: "When somebody says you have a booger in your nose, you're like, oh, I want to be around this person. I might not be happy that there's a booger, but happier than looking at it later… seeing it’s been there the whole time." [22:22]

The Friendship 'One-Page': Radical Transparency [23:21–25:17]

• Documenting Your Flaws for Connection
  Rick suggests giving a 'one-page' document to new friends or partners, explaining quirks, flaws, triggers, and value for transparency.
  • Rick: "Here's things that I'm ashamed of, but I don't want to be. I mean, faults that benefit the other person to know… as a name tag, I think would be just a really cool way of meeting people." [24:31]
  • Chris: "Here's your induction day to our friendship or relationship. Please check out section four, the bottom." [24:31]

Falling in Love with Uniqueness [25:30–27:36]

• Embracing Individual ‘Spiky Bits’
  Chris shares a story illustrating that we fall in love with people’s "non-fungible" uniqueness, suggesting we should celebrate—not hide—our oddities.
  • Chris: "What we fall in love with are all of the ways that people are not like everyone else…if you try and smooth all of those things off, you make yourself into a shape that everybody else can perceive." [26:53]
  • Rick: "Let's not be too proud and think that we shouldn't shave them down… there's an art… between self-love and the want for self-improvement." [27:36]

Rick's OCD, House Rules, and Blanket Solutions [28:42–30:51]

• Managing Quirks While Including Others
  Rick talks about his practice of requiring guests to sit on blankets due to cleanliness compulsions, but strives for compromise.
  • Rick: "It's a pain in the ass, but it's my choice. But then when people come over my place, I forget to bring a change of clothes. I'm making my thing your burden." [29:02]
  • Chris: "That’s a house condom." [29:24]

House 'Condoms,' Fart 'Condoms,' and the Comedy of Boundaries [32:57–58:03]

• Boundaries, Hygiene, & the Logic of Rituals
  The conversation becomes delightfully absurd as Rick and Chris riff on fart etiquette, clothing as "fart condoms," and the logic (or lack thereof) behind personal boundaries.
  • Rick: "Pants are fart condoms… I’ve been saying it for weeks." [57:59]
  • Chris: "You were worried about the sweat from gym clothes." [58:53]
  • Rick: "It's not that logical… I’m going to tell you, before you flush, please close the toilet seat." [58:59]

Humor as Connection, Social Anxiety, and the Role of the Bit [61:30–64:33]

• Comedy as Social Glue
  Rick shares how humor is a tool for connection and diffusing shame, relating stories about handling discomfort through bits and jokes.
  • Rick: "If you can make a bit out of something, it’s easier. I feel this way… if there's an uncomfortable conversation, there’s craft involved to saying things or setting expectations properly." [62:38]
  • Shoutout: "Buttholes have the best comedic timing." [63:54]

The Value of Self-Improvement & Acceptance [32:57–43:02]

• Balancing Growth and Acceptance
  Discussion on the dangerous extremes of self-love and personal growth, culminating in a balance metaphor (the balance board/skateboard analogy).
  • Chris: "Don’t whip yourself so much that you’re permanently miserable… But also, don’t be so accepting of yourself that you make your pathology somebody else’s burden…" [36:03]
  • Rick: "Self acceptance is a beautiful thing to do for today. Then tomorrow, look at who you were—do you like that?" [38:14]

Social Rituals, Fake Friendships, and the Need for Clear Communication [44:24–51:52]

• Small Talk as Social Lubricant
  Rick and Chris explore the nuances of obligatory small talk (e.g., "how are you?"), the challenges of sincerity, and why some social rituals are functionally necessary.
  • Chris: "Your set point is, I don't do small talk… The dance most people do in the elevator or with the dog is one that I am having to consciously teach myself… So most people have to do the opposite." [44:39]

The Compatibility Tests: Farts and The Simpsons [55:16–57:59]

• The Limits of Compatibility
  Rick presents his own unique benchmarks for compatibility in romantic relationships and friendships—shared humor, especially around fart jokes, and liking The Simpsons.
  • Rick: "People that think farting is funny and people who watch The Simpsons, I think are genuinely nice, innocent people… If you don’t think farting is funny, I know we’re not compatible." [55:38]

Fake Friendship, Boring Friendships, and Reciprocity [83:07–85:50]

• What Makes a Relationship Valuable?
  Rick questions if it’s worthwhile to persist in friendships where value exchange isn’t present and the difference between being “nice” and actually connecting.
  • Rick: "If somebody doesn’t make me laugh or teach me something… then what value are they offering me?" [81:46]
  • Chris: "Life’s too short for boring friendships in that way." [85:27]

Charisma, Conversation, and “Reverse Charisma” [85:50–94:45]

• Being Interesting vs. Making Others Feel Interesting
  Chris offers an anecdote about the difference between being interesting and making others feel interesting ("reverse charisma").
  • Chris: "Some people are interesting, some people make people feel interesting. It's a difference between being interesting and interested… a much quicker route to connection is to just get really good at asking questions…"
  • Rick: "That awareness of what they maybe think is a shortcoming is your superpower." [88:39]

The ‘Game’ Analogy: Rules, Social Bravery, and Inclusion [92:17–99:41]

• Should We Call Out the Rules or Play the Game?
  Rick and Chris debate whether openly calling out social rituals is helpful or disruptive to “game flow”—and whether it's an act of bravery or awkwardness. Rick revels in “calling out the game;” Chris sometimes prefers to influence within the understood rules.
  • Chris: "I think what I'm comparing with myself is I tend to try and achieve the same thing that you do, but within the confines of the game… I think I have less bravery socially for calling out that sort of stuff than you do." [91:27]
  • Rick: "I'm just trying to better understand what game we're playing." [93:12]

The Date Story: Radical Honesty in Practice [110:04–121:58]

• Rick’s Cringeworthy-but-Relatable Dating Experience
  Rick shares a detailed story about planning (and persistently rescheduling) a date, writing—but not sending—a highly self-aware, boundary-setting text, and the awkwardness of following through even when receiving signs he should walk away.
  • Rick (reading his draft message): “I wanted to share something before we meet because if I didn’t, I think I’d end up canceling or showing up in a way that doesn’t feel genuine. I’ve been feeling frustrated…” [116:34]
  • Chris: "I commend you for going through the 90 minute thing. I think my bitterness radar, my pissed-offness, I wouldn't have been able to reach equanimity." [120:57]

Value in Relationships: Transparency vs. Manipulation [125:30–128:50]

• Defining Intentions
  They wrap up on the idea that what seems transactional is not necessarily negative if motivations are transparent; including others in your intentions is key to authenticity.
  • Rick: "If your motives are undefined to the other person, then that's a bit like… But if you define intention, that’s honest." [125:58]
  • Chris: "It's the assumption that one person needs to coerce or convince the other… and they wouldn’t do it if they had all the information." [126:23]

Notable Quotes & Memorable Moments

• About wearing "condoms" emotionally:
  "I guess in friendships, be able to have friendships where you don’t have to wear a condom." – Rick, [05:16]
• On boundaries and feedback:
  "I want to be with people who just say, 'Rick, be quiet.' You know, 'Rick, I don’t like this anymore,' or 'Rick, do more.'" – Rick, [08:17]
• On the beauty of uniqueness:
  "Embrace the bits of you that have little tumors sticking out of them, like the spiky bits and the like little divots and stuff… if you try and smooth all of those things off, I think you make yourself into a shape that like everybody else can perceive." – Chris, [27:36]
• On farting as a compatibility test:
  "I know that we're not compatible. I know it. I know it." – Rick, [56:19]
• On real connection:
  "Who do you feel safest with isn't [a hard question]." – Rick, [54:48]

Important Timestamps

• Opening, Clothing, Comfort Metaphors: [00:00–03:00]
• Condom Analogy, Intimacy, and Presence: [03:00–05:16]
• Setting and Embracing Boundaries: [05:17–11:02]
• Small Talk & Social Rituals: [44:24–51:52]
• Rick’s Date Story—Radical Honesty in Practice: [110:04–121:58]
• Boredom & What Makes a Friendship Worthwhile: [83:07–85:50]
• Charisma & Reverse Charisma Concepts: [85:50–94:45]

Closing Thoughts & Takeaways

• Self-acceptance vs. Growth: The episode returns often to the balance between loving oneself (with all quirks) and striving for improvement—ideally through feedback from honest, safe relationships.
• Radical Transparency: Having the courage to call out the social game—whether it’s letting someone know you find small talk transparently transactional, or directly stating your feelings—can be powerful (if sometimes risky).
• Include Others in Your Truth: Delivery matters. Telling someone your real feelings or intentions is best when it also includes them—making your vulnerability an invitation, not a barrier.
• Cozy Vibes: Both host and guest agree: the more you accept and broadcast your own “cozy,” the more connection you are likely to foster.

For More Rick Glassman

• Podcast: Take Your Shoes Off (noted for its living-room, cozy atmosphere and radical candor)
• Recommended Episodes: Paul Rudd 1.0 and 2.0, David Cornerswet (Superman)
• Tour Dates & Mailing List: punchuplive.com/rickglassman

Final Words

"As long as we could both be comfortable and, like, show up as we are now, then, like, I don't have to worry about was this good or not." – Rick Glassman, [136:56]

"It feels like I can just—it's like Sunday afternoon for me. And that's, like, very, very nice." – Chris Williamson, [136:28]

This episode is a masterclass in using humor, directness, and vulnerability to build real, un-condomed connection.