#15 - Roommate Grievances with Reid Becker
Sep 19, 2023
This week I have my oldest friend and roommate Reid Becker to talk about ALL of our roommate grievances and what annoys us most about living with each other. Even if you don’t know who either of us are, I think you’ll really relate to two roommates airing out all the things that annoy each other in this way which is honestly why I think we work as roommates. We also talk about how and why we chose to live together, what we like best, and our recommendations for you and your roommates. It’s quite messy as you’d expect so no timestamps this time but give this a listen and feel free to skip around. We also go into what to do in the city if you need to switch it up, his long-distance relationship, taking the CFA, throwing a birthday party in the city, his morning routine, and other fun topics you’ll have to listen.
The Roommate Reality Check: How to Actually Live With Your Friends (Without Killing Each Other)
Honest advice from two best friends who've survived three years of living together in NYC
Living with roommates in your twenties is basically a crash course in human psychology, conflict resolution, and figuring out who's responsible for buying toilet paper. It's messy, it's awkward, and if you're doing it right, it's also one of the most important relationships you'll navigate in your early adult life.
Josh and Reed, best friends since age two, have lived together for three years across two different New York apartments. Their secret? They actually talk about the annoying stuff instead of letting it fester.
Here's everything they've learned about making roommate life work—including the grievances, the successes, and why honest communication beats passive-aggressive notes on the fridge.
Why Most Roommate Situations Fail (And How to Avoid the Disaster)
The biggest mistake roommates make: Not talking about problems until they explode.
"I think the fact that we actually openly talk about this shit is very important," Josh explains. "I think it's why we work well together. If there was something that annoyed me and I kept it bottled in, that would be way worse."
Most people assume that being friends automatically makes you good roommates. Wrong. You can be great friends and terrible roommates, or acquaintances who live together seamlessly.
The difference: Your willingness to have uncomfortable conversations about bathroom habits, overnight guests, and whose turn it is to take out the trash.
The Top Roommate Grievances (That Everyone's Too Awkward to Discuss)
1. The Bathroom Nightmares
Hair in the sink after shaving (both beard and body hair)
Not cleaning up after yourself - toothpaste splatter, hair gel on the floor
Toilet stains that stay for days because "the water will take care of it"
Basic hygiene rule: Flush the toilet, wash your hands, clean up your mess
2. Kitchen and Trash Drama
Food scraps in the sink that need to go in the trash (especially in NYC apartments without garbage disposals)
Smelly fish containers left in trash for days
Never replacing toilet paper or paper towels when you finish the roll
Not wiping down counters after cooking
3. The Overnight Guest Situation
The rule: Give your roommates at least 4+ hours notice if someone's staying over, preferably a few days.
"Having more than four hours notice would be nice. Not to invite people over if they're gonna stay over. I'm always gonna say yes because I like them all, but just having a few days notice is better than just a couple hours."
Why this matters: Apartments are small, and unexpected guests can take over shared spaces. It's about respect, not permission.
4. Personal Space Violations
Never, ever let someone sleep in your roommate's bed without asking. This is the nuclear option of roommate violations.
"That was really not cool. I should have texted or called you. Without just giving up your space. That was fucked."
What Actually Makes Roommates Work Well Together
The Foundation: Honest Communication
Start uncomfortable conversations early. It's awkward at first, but it gets easier.
"In the beginning I would get really annoyed about [dishes in the sink] and I would just do it myself, but then I'd be more annoyed because I did it myself. But now I'm like, 'yo, can whoever it is just put your shit in the trash?' Now we can just actually [talk about it]."
Shared Activities That Build Connection
Game nights with friends (Codenames, Secret Hitler)
Bowling leagues or other weekly activities
Cooking together and sharing meals
Watching trashy TV shows (shoutout MILF Manor)
Having friends over for dinner parties
The Three-Person Dynamic Advantage
Adding a third roommate can actually improve the dynamic:
Natural mediator when two people disagree
More personalities make group hangs more interesting
Prevents isolation if two roommates have issues
Practical Tips for New Roommates
Before You Move In
Have the money conversation - rent, utilities, how to split everything
Discuss guests and overnight policies
Talk about cleaning schedules and expectations
Set boundaries around shared spaces
Living Together Successfully
Address issues immediately rather than letting them build up
Be willing to admit when you're wrong and apologize
Include each other in social plans when appropriate
Respect each other's schedules and need for space
Share household supplies costs (toilet paper, paper towels, cleaning supplies)
The Cleaning Reality Check
Accept that you'll have different cleanliness standards. The key is finding a baseline everyone can live with.
Essential shared responsibilities:
Flushing toilets and cleaning bathrooms
Taking out trash (especially smelly food containers)
Wiping down kitchen counters
Replacing household supplies when empty
When to Choose Roommates vs. Living Alone
Roommates Make Sense When:
You're new to a city and want built-in social connections
You want to save money on rent
You enjoy having people around
You're good at communicating and setting boundaries
Consider Living Alone When:
You need complete control over your space
You're in a serious relationship moving toward cohabitation
You have the financial means and prefer privacy
You struggle with compromise and communication
The Long-Distance Relationship Factor
If you're in a long-distance relationship (like Reed's 4-year situation), good roommates become even more important for social connection and emotional support.
Reed's long-distance tips:
See each other every couple of weeks
Both people need to make equal effort
FaceTime regularly, not just texting
Watch shows together using Netflix Party
Send surprise deliveries (flowers, favorite food)
Red Flags: When Roommate Situations Won't Work
Avoid living with people who:
Can't have direct conversations about problems
Don't respect boundaries around guests and personal space
Have dramatically different cleanliness standards with no willingness to compromise
Don't contribute equally to shared expenses
Bring drama or instability into the living situation
The NYC Reality: Making It Work in Small Spaces
Living in expensive cities like New York adds extra pressure to roommate situations:
Space constraints mean:
Everything feels more intrusive when you're cramped
Noise carries more in small apartments
Shared spaces are even more important to respect
Storage and organization become critical
Financial pressure means:
You can't easily move if things go badly
Everyone needs to be reliable with rent and bills
Shared costs (groceries, household supplies) matter more
Building Lifelong Friendships Through Roommate Life
The payoff of doing roommate life right: Some of your closest adult friendships will come from people you've successfully lived with.
"What you did, which I appreciate a lot, is that you helped introduce me to a lot of your college friends. I really appreciate that because I feel like they like me and I like them."
Good roommates:
Include each other in social circles when appropriate
Support each other through dating and career challenges
Create a home base that feels welcoming and stable
Learn to navigate conflict in healthy ways
The Bottom Line
Living with roommates in your twenties isn't just about splitting rent—it's about learning how to coexist with other adults, communicate your needs, and build the kind of relationships that can last beyond your lease.
The secret sauce: Honest communication, mutual respect, and the willingness to call each other out on annoying habits before they become relationship-ending grudges.
Your roommate situation will teach you more about compromise, boundaries, and conflict resolution than most other relationships in your twenties. Do it right, and you'll gain friends for life. Do it wrong, and you'll at least have some great stories to tell.
Final wisdom: Flush the toilet, clean up your messes, give notice for overnight guests, and never let someone sleep in your roommate's bed without asking. Master these basics, and you're already ahead of 90% of roommate situations.
About Guyset
This post is based on an episode from Guyset: A Guy's Guide to What Should Be Talked About - a weekly podcast for guys in their twenties navigating relationships, living situations, and life's biggest questions. New episodes drop every Tuesday.
Listen and connect:
Email: josh@guyset.com
Instagram, TikTok, YouTube: @theguyset
Website: guyset.com
Have roommate horror stories or success tips? Submit them through the website or slide into the DMs.
The interview starts at timestamp 2:18
Send in any questions, things you want me to talk about, or things that should be talked about for guys in their 20s to josh@guyset.com
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See you next Tuesday.
