Podcast Summary: Man of the Year — Champions of Friendship
Episode #163: Unlikely Friendships
Hosts: Matt Ritter & Aaron Karo
Date: December 16, 2025
Episode Overview
This episode dives into the world of “Unlikely Friendships”—connections that cross the traditional boundaries of age, background, profession, race, or other social divides. Comedians and self-proclaimed “friendship experts” Matt Ritter and Aaron Karo use both humor and insight to explore why these unconventional friendships matter, how they develop, and how they benefit our lives. The conversation blends cultural observations, personal anecdotes, and listener questions, maintaining the duo's trademark banter and practical outlook.
Key Topics & Insights
1. Defining “Unlikely” or “Unconventional” Friendships
-
Opening Challenge (00:37):
Aaron quizzes Matt about historical/cultural pairs—Lincoln & Douglass, Chaplin & Einstein, Stewart & Snoop Dogg, Bernie Sanders & Cardi B—which sets the stage for the “unlikely friendships” theme. -
Defining Terms (05:00):
- Matt: “If I had to define what is an unlikely friendship, I'd say one that defies convention.”
- Traditional friendships are usually based on shared demographics, jobs, lifestyles, and interests. Unlikely friendships cross these lines.
- The guys agree “unconventional” is a more accurate term than “unlikely.”
2. Why We Gravitate Toward Sameness—And Why Breaking That Mold Matters
-
Friend Group Homogeneity (05:30):
- Most people, including Matt and Aaron, admit their closest friends are pretty similar to themselves.
- Diverse or unconventional friends usually fall into “secondary” circles but add valuable variety.
-
Benefits of Different Perspectives (07:31):
- Engaging with people outside one’s bubble is “horizon-expanding.”
- “It's just more interesting to talk to someone with a different background…just hearing a different perspective.” – Aaron (07:31)
3. Examples of Famous Unlikely Friendships
- Age, Race, Gender, Occupation (09:19):
- Snoop Dogg and Martha Stewart (“across three lines that defy whatever conventions” — Matt, 09:35)
- Entertaining quiz on their ages; surprise at Martha Stewart being 84 (10:17).
- Discussion of friendship pairs like Sanders & Cardi B, and reminders that celebrities, regardless of difference, often still share a world.
- Brief tangent on celebrity plastic surgery and “new faces” (10:47–12:24): Playful, irreverent commentary.
4. Listener Question: Navigating an Age-Gap Friendship
- Question Segment (15:31):
- A 50-something listener befriends a teen neighbor over a film project. Asks: “How do I keep the friendship positive and appropriate while still being supportive?” (15:54)
- Key Advice:
- Engage in the other’s interests; “We don’t share cultural references” is a choice, “You can watch five movies and you get a whole generation.” – Matt (18:50)
- Encourage cross-generational learning; interacting with people of different ages has tangible positive effects for both.
- Be transparent and “interface” with the teen’s parents for openness and safety (21:47–21:59).
5. How Unlikely Friendships Form
- Opportunities for Connection (29:02):
- Volunteering, sports, and hobbies as fertile ground for friendships that cut across age, SES, gender, politics, etc.
- “All the third places…are good, like your run club. You could find people at a cross section of ages and genders and politics and religion and socioeconomic status.” – Matt (29:11)
6. Challenges, Pitfalls, and Cultural Observations
-
Falling Out of Touch (29:41–30:13):
- Some unconventional friendships fade as life circumstances change (e.g., gym friends drifting apart).
- Musings on how unlikely it is for straight men to be included in queer women’s friendship circles, and vice versa.
-
Filling Gaps with Complementary Friends (31:54):
- “There's something nice about having somebody that…fills a bucket that you do not.” – Matt
- The practical benefits of friends with different skill sets, resources, or perspectives.
7. Call for Listener Stories
- Close (32:41):
- Matt and Aaron invite listeners to share their own “unlikely friend” stories.
- “DM us some unlikely friend stories.” – Matt (32:45)
Notable Quotes & Memorable Moments
-
On unlikely animal friendships:
“I like TikToks where animals aren’t just friends, where they've been adopted by another species.” – Matt (02:16) -
On friendship homogeneity:
“Your close friends...usually exhibit homogeny. Like, you’re just very similar.” – Aaron (05:30) -
On the purpose of unconventional friendships:
“They’re proof that you don’t need all that stuff to have good friendships.” – Matt (06:37)
“It's very horizon expanding.” – Aaron (26:31) -
On bridging cultural gaps:
“People who say things like, ‘We don’t share cultural references.’ That's a choice… You can watch five movies and you get a whole generation.” – Matt (18:50) -
On filling gaps in friend circles:
“I think there's something nice about having somebody that... fills a bucket that you do not.” – Matt (31:54) -
On generational respect:
“What do you think about kids when they say sir and ma’am?” – Aaron (22:30)
“I like it. Respect.” – Matt (22:35)
Important Timestamps
- Unlikely Friendship Theme Introduction: 00:37–01:10
- Defining Conventional vs. Unlikely Friendship: 05:00–07:20
- Celebrity Examples Segment: 09:19–10:28
- Plastic Surgery Side Tangent: 10:47–12:24
- Listener Question: Navigating Age-Gap Friendship: 15:31–26:00
- How to Make Unlikely Friends / Inclusive Examples: 29:02–31:30
- Skill Sets & Gaps in Friend Circles: 31:54–32:32
- Podcast Wrap & Listener Call-to-Action: 32:41–32:51
Final Thoughts
Matt and Aaron deliver a fun, insightful exploration of why unconventional friendships matter and how they broaden our perspectives. The episode is peppered with inviting asides, relatable stories, and a sincere encouragement to seek out and celebrate the “unlikely” friends in our lives.
Closing Reminder:
“Always remember, be good to yourself. Be good to your friends. Love you, buddy.” — Aaron (32:51)
Share your unlikely friendship story:
DM Matt and Aaron at @manoftheyearpodcast on Instagram