Man of the Year – Champions of Friendship

Episode #152: Rolling Three Deep
Date: October 7, 2025
Hosts: Matt Ritter and Aaron Karo

Episode Overview

In this lively episode of the country’s #1 friendship podcast, comedians and friendship experts Matt Ritter and Aaron Karo dive deep into the dynamics of hanging out in groups of three, exploring whether "three is the magic number" for friendships. Drawing from decades of personal stories, audience questions, and research-backed insights, they debate the pros and cons of duos vs. trios, offer practical advice for navigating friendship dynamics, and share hilarious anecdotes about real-life social scenarios.

Key Discussion Points & Insights

1. Sleep Training – Lessons from Parenthood

• Matt shares personal updates about “sleep training” his child, offering a comedic but poignant take on the exhaustion and the tough-love life lessons involved.
• Quote: “You have to let the baby cry all night long until they learn that nobody’s coming to save them. It’s a good lesson for life, right?” – Matt (01:37)
• This segues into broader reflections on life phases, the universality of struggle, and the need for support systems.

2. Scrapbooks, Digital Memories & The Modern Parenting Dilemma

• The hosts reminisce about childhood keepsakes contrasting them to today’s digital photo overload.
• Aaron: “Famously, my parents have this scrapbook of all my first... For Karen, nothing.” (05:00)
• They joke about losing touch with analog traditions and failing to locate photos on their phones, leading to comic banter about technology gaps.

3. Trio vs. Duo – The Friendship Optimization Debate (Main Theme)

• Key Question: Is three the optimal number for a friendship group, or is three a crowd?
• Matt: “Some might argue that the best number for friendship is three... I wanted to put that to our audience and talk about that as a topic. Is three the ideal number for friendship or is three a crowd?” (07:25)

Pros of Hanging Out in Threes

• Less social pressure: You don’t have to carry the full conversational/emotional load.
• Increased group energy and comedic banter.
• Even if one person is disengaged, the others carry on—no awkward silences.
• Travel is easier: less pressure if someone sits something out.
• Easier to coordinate than larger groups.
• Matt: “A great trio feels expansive.” (09:53)
• Aaron: “When that third person shows up, suddenly we all get charged up… Now it’s a party.” (14:53)

Cons of Hanging Out in Threes

• The classic “third wheel” or “two-vs-one” dynamic—feelings of exclusion or imbalance can arise.
• Seating and logistics can be awkward (e.g., at dinner or on planes).
• Conversation can veer into topics not relevant to all three.
• Aaron: “It’s the same thing as a sexual threesome. One person gets... No, no. Is that weird?” (11:58)
• Matt: "Isn't that healthy... that you take turns ganging up on somebody?" (12:52)
• Logistics of splitting bills and making plans can be slightly trickier, though technology (Venmo, etc.) has helped.

One-on-One Friendships

• Allow more depth, vulnerability, and attention.
• Can become “stale” or feel like you’re “on a date,” with higher energy/exhaustion demands.
• Listener insight: Some people find one-on-one draining and prefer trio dynamics.

4. Listener Question: Is Preferring Three Friends ‘Bad’?

• Question (21:05): Listener admits preferring trio hangs because one-on-one feels like too much pressure.
• Hosts validate this perspective, noting that different personalities (introverts vs. extroverts) have different social energy needs.
• Aaron: "That is a hidden benefit of the trio… if it's one on one, it's like a date. You gotta be… it's just you." (21:37)
• Matt: “Sometimes you’re just alone, one on one with people, it does feel like a date, it does feel like performing a little. I don’t know, we both have that performing gene.” (21:49)
• Ultimately, they reassure listeners there’s no “right” way to do friendship—whatever brings joy and keeps you connected is best.

5. Real-Life Friendship Logistics

• Discuss travel, concerts, and how group dynamics shift with different numbers.
• Aaron: “Definitely in the last quarter of the hang... we're hungover, it's dead silent, you know, like, we’ve covered it.” (27:29)
• Hosting and attending events—some activities (sports bars, concerts) are more enjoyable in groups of three or more.
• Matt shares news about a new “Pawn Shop” sports bar in LA, making plans for future gatherings.

6. Navigating Invitations and Turning Down Friends

• Aaron shares an anecdote about declining an invite to volunteer, consulting chatGPT for advice on how to say “no” with grace.
• They remind listeners it’s important to find “your golf”—activities you truly enjoy with friends.

7. Hilarious Commentary on Concerts and Stadium Life

• The absurdity of stadium drink prices and “single/double” upsells.
• Aaron: “Had me double-fisting vodka sodas for three hours.” (31:39)
• Discussion about concert “diet” — quarterly for them, while their friends attend much more often.

Notable Quotes & Moments

• “I think a good friendship duo feels safe, but a great trio feels expansive.” – Matt (09:53)
• “When that third person shows up, suddenly we all get charged up. Now it’s a party.” – Matt (14:53)
• “Remember that Sex and the City? Which of them has the threesome and then the other two just start hooking up and she gets pushed off the bed?” – Aaron (12:08)
• “Performing gene… it does feel like performing a little.” – Matt (21:49)
• “There is a truth to the idea of, like, if you can get a third person in on some things, it does lighten the load. It is nice.” – Matt (34:35)
• “Whatever you can do to see your buddies, right? If you have one, you know, gratitude. If you got four, great. It’s all good.” – Aaron (34:52)

Timestamps for Key Segments

• Sleep Training & Universal Struggles: 01:12 – 04:48
• Scrapbooks & Digital Memories: 05:00 – 06:49
• Technology Banter (Finding Photos, AI): 06:49 – 07:25
• Main Topic – How Many in a Hang?: 07:25 – 11:45
• Pros/Cons of Trios vs. Duos: 11:45 – 16:02
• Listener Question (“Is it weird to prefer hanging out as a trio?”): 21:05 – 22:51
• Friendship Energy, Social Exhaustion, and Activities: 22:51 – 28:54
• Stadium & Concert Anecdotes: 30:13 – 33:51
• Final Thoughts on Friendship Dynamics: 34:35 – 35:02

Summary Takeaways

• There’s no “perfect” number for a friendship group—the best is the one that works for you.
• Trios can offer an ideal mix of energy, social ease, and reduced pressure, but may present challenges like exclusion or shifting alliances.
• One-on-one hangs are best for depth; trios can “expand” the experience, lighten emotional/performative pressure, and often make outings feel more like a party.
• Whether you’re a one-on-one type, thrive in a group, or like to “roll three deep,” the real championship move is staying connected—however and whenever you can.

Authentic, funny, and loaded with practical tips, Episode #152 is a must-listen for anyone navigating the fine art of adult friendships.