Transcript

A (0:00)

Foreign.

B (0:13)

Welcome to the number one friendship podcast in the country. I'm Aaron Caro.

A (0:18)

I'm Matt Ritter.

B (0:19)

Guys, make sure to go to audible.com, the buddy system, to check out our Audible original and go to manoftyearpodcast.com to grab our merch and watch our clips on. On YouTube. Matt, today is a topic that, depending on how you define it, neither of us have had direct experience with in a few decades. And that would be roommates.

A (0:45)

I thought you were talking about cigarette smoking. I thought you were going to talk about cigarette smoking.

B (0:49)

You never smoke cigarettes.

A (0:50)

No, I know, but 20 years ago I may have had a few.

B (0:53)

Yeah, I don't even. I can't even pick. Yeah, I've maybe had five cigarettes my whole life.

A (0:59)

Oh, yeah, I've probably had, I want to say like 70.

B (1:05)

Have you noticed the proliferation of cigarette smoking on TV?

A (1:10)

It's back, it's back.

B (1:13)

I don't. Sometimes I'm like, I don't know, I'm like, it's, it's a little gross even watching it. But also like, did we. People smoke this much?

A (1:26)

Anytime I ever see a person smoking a cigarette in la, yeah. In the irl, I actually, actually have to touch their shoulder just to make sure they're real.

B (1:36)

Well, supposedly in real life, it's in again.

A (1:39)

No, I know, I'm just saying it's bizarre. But in Europe, look, I mean, I was in Europe all summer. It's like everybody smokes all the time.

B (1:48)

Can you smoke inside there?

A (1:50)

And I want to say in some places, you inside. I don't remember. I don't remember being inside. I would have obviously left instantaneously.

B (2:01)

Do you remember like, you know, arts living in New York City where you go to like a bar and then you come home and you'd have like a hole in your jacket.

Man of the Year – Champions of Friendship

Episode #181: "Roommates!" (April 21, 2026)

Hosts: Matt Ritter & Aaron Karo

Episode Overview

In this episode, Matt and Aaron return to a classic theme—roommates. They share personal stories from their days of shared housing, dissect the evolving role of roommates in adulthood, and field a listener question about navigating different maturity levels in a shared home. The conversation blends nostalgia, practical advice, and plenty of laughs, all underlining their core mission: strengthening friendship and social connection, especially during an era marked by increasing loneliness.

Key Discussion Points & Insights

The Nostalgia of Roommate Life (00:19–13:29)

Cultural Flashbacks: Before diving into roommates, the hosts take a detour into early 2000s trends, reminiscing about cigarette burns in pea coats and the shared urban experience of living in New York.
- Quote:
  
  “Every single guy from age 20 to 40 in New York in the 2000s was walking around in a black pea coat.” – Matt (02:58)
Personal Roommate Histories:
- Matt: Frat house living at Binghamton, an off-campus stint on “Crack Row,” law school (roomed with a clean-cut classmate), a few short-term post-grad situations, and finally settling into partnerships.
  - Standout moment: The infamous stool sample incident with his roommate Brad.
    
    “I left them in the bathroom... I was brown-bagging it.” – Matt (08:09)
- Aaron: Managed to have a single room all through college—unusual for his social group. Shared a place once with a friend (Brian) post-college, which led to the legendary “toilet paper wars of 2003.”
  - Quote:
    
    “That soaked in the OCD, where I could never...you can never go back from that. You can never go.” – Aaron (08:50)
Roommate Quirks: Matt’s laid-back, sometimes messy approach is admitted with comic self-deprecation—including leaving diapers out and eggshells in the fridge.
- “It falls under the same logic...alright, I gotta go do the next thing. This has been situated to my satisfaction.” – Matt (12:05)

Roommate Dynamics and Friendship (13:29–19:20)

Do Roommates Make Best Friends?
- Roommates can either become lifelong friends or stay friendly acquaintances. There’s inherent vulnerability and bonding, but not every pairing goes deep.
  - “It has the potential to turn into a lifelong friend, sharing formative years in your life.” – Matt (13:29)
Risks of Moving in with a Friend:
- Matt cautions that living together can strain even close friendships. Cleanliness, schedules, social habits, noise, and finances are frequent friction points.
  - “There are a lot of friction points with roommates that you don’t have in a friendship that lives outside of a shared apartment.” – Matt (15:20)
“Should I Move in with My Friend?” Checklist:
- Key questions before moving in:
  - Cleanliness compatibility
  - Social vs. solitude preferences
  - Sleep schedules
  - Who pays bills?
  - Routine overlap
- “Who’s paying the bills? Financial frictions, potentially, yes.” – Matt (17:16)
Changing Trends: Roommates in Later Life:
- The economics of big city living and changing social norms mean more people in their 30s and 40s have roommates—sometimes by necessity, sometimes by choice.
  - “The trend: roommates are getting older and older because, you know, of the economy and it’s expensive, especially in big cities.” – Aaron (18:15)
- It’s okay if your roommate is an acquaintance, not a best friend, as long as boundaries and expectations are clear.

Listener Question: How to "Age Up" a Party House? (21:56–32:08)

[21:56] Listener’s Dilemma:
A 36-year-old, living with two close friends, finds that one roommate still loves late-night parties and crashing guests—turning the apartment into a "crash pad" reminiscent of their 20s. The listener wants to ask for a more mature, quieter environment.

Key Insights & Advice

Upfront Conversations are Crucial:
- “When moving in with somebody, all these questions should be on the table. Don't get awkward at the beginning... it will come back to haunt you later if you never said specifically, like, hey, guests. What’s our policy on guests?” – Matt (24:32)
Diplomatic Communication Strategies:
- Frame questions kindly: “What’s our policy on guests?” instead of demands.
- Approach one-on-one first (avoid making the person feel ambushed by a group).
- Gauge cleaning habits, entertaining expectations, and sleep schedules early.
- If mismatched, sometimes the only solution is a tough, honest talk.
  - “You have to have the conversation. There’s no way around it.” – Matt (26:17)
Honest Assessment:
- Sometimes, differences in lifestyle just aren’t reconcilable.
  - “Ultimately, it’s not going to work out, truth be told...you’re not aligned as roommates.” – Matt (28:53)
- Consider lease and legalities: If you can’t find middle ground, it might be time for a move.

Memorable Listener Segment Moments

Epic New York Apartment Stories:
- Tales of room dividers, tight spaces (“the Russian nesting doll of rooms”) and the exhilaration of demolishing faux walls after a lease ends. (22:34–23:58)

Broader Lessons & Takeaways (32:19–33:43)

The Friendship Upside:
- Even if you’re not best friends, having a roommate reduces loneliness and offers the chance to expand your social circle via “friend extension” (meeting roommates' friends).
  - “It’s a good built in social...I’d rather have somebody to live with even if they’re not best friends, than have nobody.” – Matt (32:52)
Expectation Alignment is Everything:
- “A roommate has potential to be a lifelong friend or an outer fringe friend or just a person you get along with. But that's only if your expectations aren’t aligned.” – Matt (32:19)
Social Trends:
- The resurgence of adults living with roommates can help address the “friendship recession.”
  - “Given our state of loneliness in the country, the fact that roommates are kind of back on trend...even for slightly older people, I think is a good development.” – Aaron (32:37)

Notable Quotes & Timestamps

[02:58] Matt: “Every single guy from age 20 to 40 in New York in the 2000s was walking around in a black pea coat.”
[08:09] Matt: “I left them in the bathroom...I was brown-bagging it.”
[08:50] Aaron: “That soaked in the OCD, where I could never...you can never go back from that. You can never go.”
[13:29] Matt: “It has the potential to turn into a lifelong friend, sharing formative years in your life.”
[15:20] Matt: “There are a lot of friction points with roommates that you don’t have in a friendship that lives outside of a shared apartment.”
[18:15] Aaron: “The trend: roommates are getting older and older because, you know, of the economy and it’s expensive, especially in big cities.”
[24:32] Matt: “When moving in with somebody, all these questions should be on the table....”
[26:17] Matt: “You have to have the conversation. There’s no way around it.”
[28:53] Matt: “Ultimately, it’s not going to work out, truth be told...you’re not aligned as roommates.”
[32:52] Matt: “I’d rather have somebody to live with even if they’re not best friends, than have nobody.”

Structure & Flow

The hosts move fluidly from personal nostalgia to practical, actionable advice, keeping a humorous, open-hearted tone throughout.
Listeners are encouraged to share their own stories, especially about the new “post-college roommate” trend.

Final Thoughts

“Roommates!” is an episode packed with laughs, memories, and frank advice. Matt and Aaron’s chemistry shines as they tackle the enduring ritual of sharing living space—recognizing all its potential for lifelong friendship (or disaster). Whatever your age or city, the keys are communication, clear boundaries, and embracing the sometimes chaotic, always memorable, world of roommates.

For more friendship hacks and stories, visit manoftheyearpodcast.com or follow @manoftheyearpodcast on Instagram.

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#181 - Roommates!