#181 - Roommates!

Summary

Man of the Year – Champions of Friendship

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

Hosts: Matt Ritter & Aaron Karo

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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.

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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.

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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)

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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)

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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.”

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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.

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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.

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

Transcript

[A]

Foreign.

[B]

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

[A]

I'm Matt Ritter.

[B]

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]

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

[B]

You never smoke cigarettes.

[A]

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

[B]

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

[A]

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

[B]

Have you noticed the proliferation of cigarette smoking on TV?

[A]

It's back, it's back.

[B]

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]

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]

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

[A]

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]

Can you smoke inside there?

[A]

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]

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.

[A]

My mom's still pissed about that. Yeah, because I was still on the mom buys the J, you know, not JCPenney. JCPenney in middle school, high school. But I think in the 2000, mom was buying me the J. Crew black trench coat. Oh yeah, that was classic.

[B]

I think you mean like a pea coat.

[A]

Pea coat. I did mean peacoat. I did not mean trench coat. I was never a trench coat guy. Were you?

[B]

No, but I really want to be one Our, our buddy, our man of the year buddy. Jay, I think has one and it's like, looks really cool.

[A]

You don't want to be a trench coat guy.

[B]

La. You can't really because the weather, it just, you seem like a. Yeah, you

[A]

see Me, but two things. One is, it's really for taller folks. The trench who? Can we just talk about the fact that you just hit me when you said peacoat. Every single guy from age 20 to 40 in New York in the 2000s was walking around in a black pea coat.

[B]

I'm not gonna lie. I still have mine in the closet.

[A]

You do now? Once I got that cigarette singed right through, my mom was all pissed. She's like, I'll never buy you another pea coat. I don't think she ever bought me another pea code from J. Crew after that. And then they went out of style at some point. I think they're back in now, but, like, I don't think people younger understand every single one of us. We're the exact same thing.

[B]

I think they do it now, too. It's just a different jacket.

[A]

That's right. Maybe that's right. What do they wear now? Starter jackets. That'd be awesome if they're all back.

[B]

Is Starter still, like, exists as a company?

[A]

Starter.

[B]

It was amazing, too, because you think about style or any trend when we were growing up, like, there was no Internet. No.

[A]

You just saw people and you were just like, I gotta have it. You saw people and. But. But the cigarette thing is hilarious, because I would love to do a poll from our listeners. How many of you who had the pea coat also had the cigarette burn in the. In it?

[B]

Oh, if you were living in the city, if that was a very certain time, you have cigarette holes, cigarette burns in your.

[A]

Brutal. Because there's nothing you can do.

[B]

No, it can't be fixed.

[A]

You put a patch on it. So. So actually, Jesse, I bought her a really nice limited edition Marc Jacobs Relatable Matt coming out here. Purse in the early. What do you call them? Teens.

[B]

20 teens. Yeah.

[A]

And I think we were out for Bombay Claire's birthday, and Jesse put her purse on next to a candle and a little hole, like, right in the top middle of the purse. So we actually had them, like, create. We went to a leather upholstery store and create, like, a fake new square with the same color on top. So it became like a one of one.

[B]

That's interesting. Were you upset?

[A]

Well, no, I actually thought it looked cool. You know, I was like, oh, this is actually. We'll turn this into a. Like, oh, this is even fancier. So you don't have the one with the little square on the top.

[B]

Does Jess. I mean, you leave your keys, lose your stuff everywhere. Does Jess lose stuff?

[A]

Very out of character for her to Ever do any of that stuff?

[B]

Well, of course. I mean, Jeff's not going to be happy that I bring this up. I don't know if you recall the famous story in Coachella. We were watching Beyonce, one of the greatest concerts of all time, and Jeff's wife lost her purse.

[A]

Had he, had. He had to order her like a 400 limo ride back or something, whatever.

[B]

We all. This is how good friends we were. She had to go search for the purse. So we all went like 12.

[A]

Oh, my God. That's horrible decision. That's amazing. That's friendship.

[B]

Yeah. Well, speaking of early aughts, I guess that's a pretty good segue because the early aughts were the last time that I had a roommate. And it's come up sometimes a few times. It's actually going to come up on our listener question. That is a very specific friendship relationship. Right. You're literally living with your buddy. Some people live with strangers and then become friends. Or some people live with people who they're not friends with. A lot of pitfalls, pros and cons. What is give us. Give our listeners your roommate a history from college to the present.

[A]

Okay, so moved out of the frat house with one other guy in college to like off campus and lived on crack row, which was a mistake.

[B]

In Binghamton, it's really called Crack Row.

[A]

Yes, yes. Because Binghamton's an old kind of rundown city that used to have like IBM and, I don't know, Kodak. And once those things go, everything just kind of turns to see the townies, the drug addicts. So that was dicey. Dicey. And then law school, I lived with a. A really nice guy named Michael who I was a Probably like too loud party. He was like a clean cut kind of guy in law school.

[B]

How'd you meet him?

[A]

No, just. He was in my section. Yeah.

[B]

Yeah.

[A]

And then post law school, New York, I lived with Brad. Triplet Brad.

[B]

Yeah, a couple years.

[A]

And then with girlfriends ever since.

[B]

So Brad, your last roommate, Brad has

[A]

to be my last. I had a hot second. No, no, I had a hot second with Jordan in L. A. Barry, and like, you know, months at a time. So probably Jordan in LA 2009.

[B]

I mean, when you live with Brad, that's also home to the funniest story, my favorite Matt story ever. When you, you know what I'm talking about?

[A]

I have no idea. It could be anything.

[B]

It's not that bad. It's when you had to. You had a stomach problem and you had to test your Stool samples.

[A]

Oh, yeah, yeah. Stool sample testing. And I left them in the bathroom. It's bedroom 80.

[B]

Collect his tool samples in a brown.

[A]

Where would you have me keep them?

[B]

It's just that you said. You told me you were brown bag in it. That was the funniest thing I've ever

[A]

heard in my life. We had some good times. Oh. Then I had a roommate, Adam, writer, writer guy out here. So 2009 was the last time. How about you?

[B]

Yeah, well, I had a crazy run because in college I had no roommates.

[A]

How did that happen?

[B]

I had a single. The freshman in the. In the quad at pen. You can have. There's some singles. Then in the fraternity house I had a single. And then in our off campus house. I mean, we lived in a house,

[A]

but this is so Cairo to go through all of the seminal experiences of that age bracket alone in his own room.

[B]

Yeah. If I hadn't had the single freshman year, I think that like really like that soaked in the ocd, where I could never. You can never go back from that. You can never go.

[A]

I think. Yeah. Do you think the OCD was formed there? It was always in you. And it just. I'm saying, like. No, no, no.

[B]

It was in me, but it was like sealed in.

[A]

Cemented. Yes, sealed in. In the stuff that seals those. Like, you know, those ants that we find millions of years later in the SAP. Like the.

[B]

In amber.

[A]

Amber. Amber. You got sealed in ocd, Amber. Ocd, Amber alert for this guy.

[B]

And then. And then famously, when I was working on Wall street, live in the city, early aughts, I'd live with our buddy Brian.

[A]

Toilet paper wars of 2003.

[B]

Yes. I wrote about extensively in ruminations. We would. I think we refused to get toilet paper.

[A]

Who backed down?

[B]

I'm sure it was me because at one point I was living. I was working from home. I was like original work home guy. So I needed that. And that's the first, last and only roommate I've ever had,

[A]

by the way. I was just thinking of backing down, like that kind of stuff. Like Jesse backed me down into putting the diapers away properly in the diaper caddy

[B]

properly or putting them away at all.

[A]

Yeah.

[B]

So wait, let me. Let me try to tell you what I think. First of all, I don't even. I'm not even getting into that. Let me. The diaper caddy is the thing that you. You throw out the diapers, right?

[A]

Yeah. No, that's where you're supposed to put up.

[B]

Yeah, right. In my understanding, I've never used it. Like it's got some sort of technology that sucks the smell away.

[A]

Yeah, it's generally. It's sealed pretty nicely.

[B]

But. But is the diaper caddy just a soup. Futuristic garbage can?

[A]

Yes.

[B]

And just. It seals closed.

[A]

Yes.

[B]

So when you open it, does the stink come out?

[A]

Not really because it has a small

[B]

hole, so you're smushing. So how do you put a diaper in wrong in a diaper caddy?

[A]

Well, I was, I wasn't putting him in.

[B]

So what were you doing? Throw up, putting him under the sink like brown baggage. I was just.

[A]

I was just. They were just ad hoc situation.

[B]

You left them out?

[A]

Yeah, I was leaving them out.

[B]

That's horrid.

[A]

Yeah. Well, here's what happened in my defense, okay? Maybe there's some dads out there that you know are in the sitch. You're changing a baby on the table. Okay. And you're changing the dirty diaper. You're wiping the dirt. I change a lot of diapers. I'm a very active dad and I

[B]

give you, Give you credit for that.

[A]

But originally my thesis was, you know, I will go back and put it in the caddy later because I'm changing him, I'm putting him in his clean clothes and now we're just off to the races and we're doing stuff. So I was just kind of like, lead them, leave them as they lie. And then I guess my wife and my nanny were, you know, picking up after me.

[B]

So not even like rolled up. They were just opened up.

[A]

They rolled up.

[B]

Yeah. I mean, that is a very matte. Like, I couldn't. I couldn't go play onto the next thing without discarding.

[A]

It's the same reason I put the eggshells back in where they lay. I was just gonna say it falls under the same logic of like, movement of like, all right, I gotta go do the next thing. This has been situated to my satisfaction.

[B]

Yeah, I'm sure.

[A]

It's insane.

[B]

Yeah. Oh, I believe it's episode 67. Guys, check that out. Matt explained that when he makes eggs, he cracks them open. Then he puts the empty shell back in the carton back in the fridge.

[A]

My sister didn't even know I did that. She was horrified.

[B]

I mean, it's just.

[A]

But anyway, so now. But now I do put the. I do put the used diaper into the diaper caddy.

[B]

Wow. Bravo, Matt. He throws away a dirty diaper. Just 46 year old.

[A]

I had to be shamed into it, though, by my roommate, by my Roommate.

[B]

Now, do you consider your wife your roommate?

[A]

No. I mean, that's absurd.

[B]

Yeah, that's absurd. Um, so. So roommate. You know, we have a lot of listeners who have roommates. Like, first of all, you know, you sort of made fun of me for having the singles in college. I would assume that you, Matt, think that, like, there's a lot of upside to having a roommate.

[A]

Well, yeah, I think a lot of people's roommates become their best friend for life. You know, like there's a built in. It's not just a built in friend. It's a built in vulnerability, camaraderie, built in, same schedule. Like, there's so much stuff where it could turn into. Look, I'm not saying it always does. Sometimes it just is one and done. What it has the potential to turn into a lifelong friend. Sharing informative, formative years in your life.

[B]

We talk about in the buddy system, level up. Moments, traveling with a friend, meeting their parents, living with a friend. Yeah, I mean, that's some. You really get to know somebody.

[A]

And I'd say, look, you know, there's different types of roommates, right? There's like. What I'm talking about is the best case scenario is it's a roommate that becomes a best friend. But sometimes it's just. I had a functional roommate in law school, you know, friendly, not like too deep about it. We were coexisting, like friendly, kind of living our own lives. We were adult. That was like an adult roommate situation for sure.

[B]

Share a bathroom or. No.

[A]

No.

[B]

So what, just a shared common room?

[A]

Yeah, pretty much.

[B]

Yeah. Yeah, yeah, yeah. I mean, sharing a bathroom, that's real. That's real next level stuff.

[A]

Yeah. So, I mean, you know, like, I think there was a lot of positive. But I, you know, I think the idea is, you know, you should look at a roommate as. You can look at it however you want. You know, you don't have to force it into best friend, but the possibility is there to have all the built in great stuff about friendship.

[B]

Do you think there's ever. You should, you should have pause. I should give you pause if you have a bestie and you're like, let's move in together, like, it could ruin the friendship.

[A]

Yes. Because there are a lot of friction points with roommates that you don't have in a friendship that lives outside of a shared apartment. Don't you think?

[B]

What kind of questions do you think you should ask a potential a buddy or ask yourself before you move in with a bestie?

[A]

Okay, well, obviously it's the clean dirty. Right. Are we, like, the same level of cleanliness? Are we the same level or within range of solitude versus partying?

[B]

Sound.

[A]

Sound. Sound.

[B]

Right.

[A]

Yeah. Sound. Right. Like, are we, you know, are we able to, like, share a space in the way that makes us both in our headspace, feel okay?

[B]

So. So best. Best friend Mike, you know, he used to live with our buddy Drew.

[A]

Yeah.

[B]

And best friend Mike is quite clean. He's a. He's a KO And Drew is a mat.

[A]

Right.

[B]

And.

[A]

Right. I'm not a great. I'm not a great roommate. I would. I wouldn't. I wouldn't deny it.

[B]

You have other qualities. That's not one of them.

[A]

Yeah.

[B]

Although it would be pretty fun. It would be a fun house to live in.

[A]

Yeah. Yeah, yeah.

[B]

But anyway, so Drew would never clean anything up, and, like, Mike had to literally make, like, a chores list. I mean, they were probably, like, 30. Yeah. And I'll never forget. I think I have a picture of it. He titled it It's Come to this. And. And it was just like, it's come to this. Yeah. Like, you got it. Who takes the garbage out? You know?

[A]

Yes. It has a potential to rock a healthy, otherwise healthy friendship, for sure.

[B]

Yeah. Yeah. Also, it's like, morning person versus night person is a big. Is a big deal.

[A]

Right? Your routine. Right?

[B]

Your routine.

[A]

What is your overlap? What is your routine? Do you. Your routines mesh? Do they overlap? Are they completely at odds with each other?

[B]

Who's. Who's paying the bills?

[A]

You know, financial frictions? Potentially, yes.

[B]

Yes.

[A]

I think when you're younger and, like, here's the question. What do we. What are we asking this for? Like, what. What person are we? Because there's a different question. Who are we asking this for? Like, should you live with somebody? You know? If you're saying, hey, I'm going to college. Should I live with my friend? Yes. Yes. The upside's too high.

[B]

What do you think about the fact that now, or maybe then, too, you could choose who you live with in college where it used to be kind of random.

[A]

Right. I think. Look, I think there's definitely something to be said for random, because you learn a lot of lessons about how to live with other. How to. How to be compromising, how to be flexible, how to be respectful. Dare I say, first time in your life, you learn how to be respectful of other people's space. You probably don't think about it. Right. Pre college, random person. When do you need to, like, learn how to be respectful? Other people's space? And boundaries, really physically, like physical spaces. Not that often.

[B]

But I also bring this up because now the trend, roommates are getting older and older because, you know, of the economy and it's expensive, especially in big cities.

[A]

Yeah.

[B]

Like, there's people who, you know, in their 30s and 40s just love roommates. And some love it. I mean, there's an article New York Times called Roommates Forever.

[A]

Yeah. I think it's a good look. Obviously, financially you have to do what you have to do. So, you know, not gonna say, hey, don't live with somebody. If you need to be able to live in a city, you live with somebody. And in New York, that's what a lot of people do in these big cities with small spaces. Super expensive. Your job is there, whatever, do it. And look, that doesn't have to fall under the rubric of like, oh, I'm doing this to make my best friend like, you're doing it because it's functional and it works for you. But you could also make it work for you, you know, in ways that don't have to be a best friend way. Right. Like there's like, you could, you know. Let me ask you this. Do you think you can delineate in a way that doesn't cause friction if you're like, I want to put you in the, you know, acquaintance friend bucket where I invite you out sometimes, or do you think that gets confusing?

[B]

It really depends on what the other person. Thanks. The other person has their own life, then that's not a problem whatsoever. You guys are going to be homies, right?

[A]

The expectation going in has to be clear.

[B]

Should we, should we take a listen question?

[A]

Yeah.

[B]

All right, we'll be right back with a listener question.

[A]

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[B]

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[C]

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[B]

That's nationaldebtrelief.com okay guys, this is asking for a friend. If you have a friendship question or ethical dilemma, send it to us on Instagram at Man of the Year podcast and we will answer it on the show. All right, Matt Dear Matt and Cairo, I'm 36 and share an apartment with two close friends, partly because rent is brutal, but also because it's genuinely really fun. The problem is one of the friends treats it like we're 23 with late night parties and random guests crashing on the couch. Is there a polite way to say I love living together but can we age this house up a little bit?

[A]

Oh, I love this. It made me by the way, it reminded me my sister lived with two Conor Andos in New York in a one bedroom that they split twice. I don't. I don't know if people understand how small some of these New York apartments are. One bedroom split twice.

[B]

I mean, I've never heard I split. I split once, twice. How's that even physically possible?

[A]

Split into thirds? Kim's was the middle room and it was just a bed and she had a whole different. She was doing jewelry at the time, so they had all these, like, shelves with jewelry. I think they had one closet elsewhere for all of them. And we call. I called it like the Russian nesting doll of rooms. Like, inside her room was another room. Inside that was a smaller room.

[B]

Well, I think they call that like a railroad. So you had to actually go through her room to get to the other rooms?

[A]

No, no. But it was a very thin hallway, and they divvied up the bedroom into thirds against it. So they put two little doors. You know, it's. It was nuts when.

[B]

When me and Brian had had the. The. The fake wall, then we moved out. We had to take it down. And you should have seen these two. The least handy people ever with, like, a sledgehammer that's trying to knock.

[A]

That's got to be fun.

[B]

It's pretty fun. You know, I hammered.

[A]

I once hammered, like, a pass through window in our old house through. It's really. It's a good feeling. If you ever get the chance to hammer through a. Like, a fake wall, do it.

[B]

But how do you. How do you make it square on a pass through window?

[A]

I don't know. That was the contract. That part. I just. He just let me take the mallet.

[B]

Oh, you just did a wall. You said a hole. Okay.

[A]

He let me do the demo. Yeah, he let me. He's like, you want to do it?

[B]

I'm like, yeah, you make it seem like you did it. But no, a guy was. A guy was standing there.

[A]

He handed me the mallet.

[B]

Oh, my God.

[A]

Okay, so. Okay, so what's the question? Oh, age up.

[B]

Yeah. Like, we're treating this like a crash house or a frat house. And, like, we're 36 here.

[A]

Right. So it sounds like the first mistake was this convo didn't happen upon moving in.

[B]

Maybe he didn't know because they never lived together.

[A]

Right. So just for our listeners, number one is, when moving in with somebody, all these questions should be on the table. Don't get awkward at that beginning. Don't feel shy at the beginning, because it will come back to haunt you later if you never said specifically, like, hey, guests. What's our policy on guests? Yeah, because everybody has the same right. Unless this person's subletting from you. Everybody has the same right to, like, bring guests over.

[B]

I like that euphemism. What's our policy on guests? Because that tells you a lot.

[A]

A lot.

[B]

What other youth. Like, what other questions that. Because that's a very diplomatic question. Yeah, like, are you gonna. Are we gonna be entertaining a lot?

[A]

Yeah, are we gonna be entertaining a lot? It's a good one. What's our policy? I guess, are we gonna be entertaining a lot of. What's your general sleep schedule?

[B]

Ooh, sleep schedule is good.

[A]

You say it that way so it's like. Or you could be like, look, I don't want to. I don't want to. I don't want to disturb you. What's your. You can say it that way, like, I don't want to disturb you. What's your sleep schedule? Oh, don't worry about me. I stay up till 2am Right, right.

[B]

You could be like, do you want to like, split like a housekeeper? Oh, no, no, I'm pretty clean.

[A]

That's a very good one because you should have a housekeeper regularly. A shared space.

[B]

Yeah.

[A]

What do you think the regular amount of time for a shared space cleaning person should be frequent?

[B]

Brian, I. It couldn't have been more than once every couple weeks.

[A]

Gotta be every two weeks.

[B]

Yeah, I, I have. I'll have to ask him anyway.

[A]

So. Yeah, I mean, you know, it's aging. Aging up. Look, you just have to have the conversation. There's no, at this point, there's no way around it without just ripping off the band aid.

[B]

Now that they live together, you have

[A]

to have a tough conversation, in my opinion. Now you have to have a tough conversation. There's no way around. Because you need to. You need to fix this and you need to fix it immediately.

[B]

Right? Right. Late night parties and random guest crashing on the couch. Seems pretty fun.

[A]

Yeah. And I think you say, hey, can we talk about our guest situation?

[B]

Yeah, yeah. Also, there's three. There's two friends, and one of them is. So you need.

[A]

You don't want to feel like you're attacking them. So maybe you try it one on one first. Because if you just go, hey, we've been talking about you, that may unleash a defensive response.

[B]

Okay. Because I was gonna, I wasn't gonna say that. But you should definitely strategize with the

[A]

other 100, make sure they're on. On board with that too.

[B]

Yeah, yeah, yeah, yeah, yeah. You don't want to do that intervention.

[A]

Right, Exactly. So I think that's the, that's the way to. The best way to do it is the nonchalant, like, we're not attacking you, but would love to discuss this because it is a problem for me.

[B]

Have you ever done an intervention?

[A]

So I don't think so. Oh, yeah, yeah, I did do one, Mikey.

[B]

Yeah, yeah. Put it all out of her mind. Yeah, I think that's right. I mean, I think this flows with all the other, you know, advice we've given, you know, for the past four years or so, which is that you need to have a conversation, and otherwise they're gonna have no idea. They're gonna think it's fun.

[A]

Right.

[B]

You know, the other question is, who's on the lease? Like, if they're like, this is my part, you know, like, I'm on the lease.

[A]

Exactly. That. That's. That can be a major, major issue. But, you know, look, here's the truth. If somebody is like that in their, you know, and they're in their 30s and that's what they're doing, they're living, like, life, like their 20s. Like, you going, hey, let's age up the apartment. Let's have more wine club nights. Like, that's not what they're about. You're not. You're not aligned as roommates because, you know, look, imagine you're that other person, right? You're in the middle of a phase where you're partying, you're sleeping at random places, you're having random friends come back and, like, you know, whatever, drink, smoke, whatever. That's what you want to do at this point in your life. You feel you're entitled to do that, Right? Obviously, this person feels they're entitled to do that, and they probably want to continue doing that. So I think ultimately it's not going to work out, truth be told. I just don't think it's going to work out.

[B]

This may be the. Yeah. This may be the first listener question ever where we were just like, it's. There's no hope.

[A]

Yeah. Because. Because that's what that person wants to do. It'd be different if you're in a relationship and you're like, you know, like, when Jesse was like, matt, I don't want you to drink it that much anymore in my. You know.

[B]

Yeah.

[A]

And I was like, oh, okay. Yeah, I guess I shouldn't be doing that anymore.

[B]

Yeah.

[A]

Like, you're not in charge of that person's life. If they want to be doing that, you know, they're fully entitled to be, you know, living hard and partying hard. There's not entitled to do it in a way that disrupts your. Your piece. So you either have a condo and say, hey, can you. You know, can you have. Can you go to your friends. Places if it's past a certain hour?

[B]

Or let's. Let's let's look at it from the other person's point of view.

[A]

Yeah.

[B]

You're living with your two best friends. You're, you know, we don't know what their jobs are, but you're going out at night, you're. You got friends crashing.

[A]

Yeah.

[B]

You be like, hey, man, my friend's going to crash. Is that okay? Like, I feel like you.

[A]

Obviously they should be. Yes, they should be cognizant, but clearly they're a little blacked out to what's going on. If both their roommates are living a quiet life of like, hey, we watch, you know, our HBO Netflix shows at 8 and we're out and then suddenly, three hours later, somebody's barging in with a crew.

[B]

It's the worst.

[A]

It's the absolute worst.

[B]

One time when I was living with Brian, he was like, oh, I gotta, like, I got an early night. I got a bit early morning the next day and I went out. He's like, just keep it down. I went out and I think I randomly ran into some friends on our block. And I was like, come back. And we just, we literally, he's like, I Talked to you 20 minutes ago. Next thing is.

[A]

Oh my God, that's awesome. By the way, my roommate Jesse always says if I'm out with the boys, like, you guys sleep downstairs.

[B]

You're saying your wife sleep downstairs?

[A]

Yes.

[B]

Yeah. Because is, Is it like. Yeah.

[A]

Woken up? People don't like being woken up. It's a, it's. It's very frustrating when you're asleep.

[B]

Right. But you also don't move very stealthily.

[A]

The worst. I'm the loudest. We have wood floors. They creek. There's nothing I can do.

[B]

Yeah, you're knocking into stuff left and right.

[A]

You're always knocking into stuff. I'm always knocking into things. Things.

[B]

You listen to your podcast.

[A]

I'm full on speaker. Yeah. Oh, Jesse. Now the new thing is actually she has me set the alarm off outside before I even come in. She doesn't even want me coming in and futzing with the alarm because I can do it remotely.

[B]

Okay. Yeah. Yeah. Well, that just reminds me of the one man of the year when I came back to my parents house and I could not figure. I was so drunk, I could not figure out the alarm.

[A]

Nobody can ever figure out somebody else's alarm while drunk. It's impossible.

[B]

Yeah. I think we actually talked about this like three years ago. We haven't.

[A]

Yeah, I mean that's like. That seems like something from Saw. You have one minute to figure out your parents alarm or you die. Okay, I'm dead. Just shoot me. Just kill me because I'm not going to be able to figure out my parents alarm. Sorry, just cut my eyeball out. Saw.

[B]

All right, do we answer this question?

[A]

I think so. I think, you know, you're gonna have to have the convo. You should have had it up front. You don't have to make it like don't put them on the defensive. You don't be like you're immature. You don't have to talk down to them about it.

[B]

All right, guys, this was asking for a friend. If you have a friendship question, send it to us on Instagram and we will answer on the show. Matt, any final roommate thoughts?

[A]

A roommate has potential to be a lifelong friend or an out outer fringe friend or a functional, you know, just person that you get along with. And there's space for having socialization with your roommate. Or it can be a total nightmare. But that's only if your expectations aren't aligned.

[B]

Yeah. And given our state of loneliness in the country thing that we're trying to address in this pod, you know, the fact that roommates are kind of back on trend, even for slightly older people I think is a good development. Yeah, it's a good built in social.

[A]

I'd rather have somebody, have somebody to live with even if they're not best friends, then have nobody.

[B]

Right. At least you're having a conversation. You have a little, you know, interaction with some people. They have some. They. I mean they know people. So I think it's good.

[A]

Yep. Yeah, we didn't even talk about that potential of, you know, roommate, friend, friend extension. I've had many of those in life in New York.

[B]

Yeah.

[A]

Where like your friends, roommates become your friends. Like that's definitely something that happens.

[B]

Oh yeah, I thought you were going to say roommates romance.

[A]

I mean that's happened for people too, I'm sure.

[B]

Yeah. Yeah, yeah, yeah. Well guys, let's hear your roommate stories. Especially if you are living with someone sort of in a post college, a little bit older scenario. Because that's like the new, the new thing. Guys, thanks so much for listening. Always remember, be good to yourself. Be good to your friends. Love you buddy.

[A]

Love you, buddy.

[E]

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[B]

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