Guyset

If you're feeling completely lost in your twenties right now, this episode is for you. I saw this guy's TikTok about feeling directionless at 25, and it hit me so hard because I've been feeling the exact same way. So I wanted to share something that's been helping me navigate this weird post-grad phase we're all going through.

What I'll Share With You:

• The "Rule of Thirds" that changed how I think about my bad days (spoiler: you're only supposed to feel good 1/3 of the time)
• Why ages 22-28 feel so freaking weird and why that's totally normal
• How I've started categorizing my days to stop spiraling when things feel off
• Why we as guys never talk about this stuff (and why I think we should)
• My strategies for getting out of my own head when I'm overthinking everything

What Inspired This Episode:

• A viral TikTok from a 25-year-old guy who perfectly captured how I've been feeling
• The best advice from Emma Grede (Shark Tank) that applies perfectly to life transitions
• Keke Palmer's wisdom about life's ups and downs
• My own recent struggle with feeling like everyone else has it more figured out than I do

This Episode Is For You If:

✓ You're a recent college grad feeling completely directionless

✓ You're in your 20s wondering what the hell you're supposed to be doing

✓ You feel like you're the only one struggling while everyone else seems fine

✓ You're tired of pretending you have it all together

Topics I Cover: post-grad depression, quarter-life crisis, men's mental health, life transitions, twenties anxiety, career confusion, relationship uncertainty, personal growth, getting out of your head

I get really honest about my own bad days, my tendency to overthink things, and how I've been dealing with the pressure to have my life figured out by 25. This isn't me pretending I have all the answers, it's just me sharing what's actually helping me get through this weird time.

New episodes every Tuesday covering what we actually need to talk about as guys in our twenties.

Subscribe, give this episode 5 stars, and leave a review!

• Ask Me Anything: guyset.com
• Instagram: @guysetpodcast
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Email: [email protected]

See you guys next Tuesday!

Today I'm joined by Alex Joseph Grayson who is currently playing Dallas Winston in Broadway's hit musical The Outsiders. This conversation blew me away as Alex opened up about the reality behind one of Broadway's most physically demanding roles and shared his knowledge that will resonate with anyone chasing their dreams.

What we dive into:

The Real Broadway Experience:

• What it actually takes to perform 8 shows a week in one of Broadway's most physical roles
• How Alex stepped into The Outsiders mid-run and made the character his own
• The intense workout routine and recovery process he needs just to survive the show
• Honest talk about injuries and the athlete-like demands of commercial theater

Rejection and Resilience:

• Alex's journey from discovering theater at 19 to landing on Broadway at 36
• His powerful mindset shift: "their loss" when facing constant industry rejection
• The "Four Daily Wins" system he uses to build self-worth
• Why creating value outside the commercial system is essential

Mental Health in High-Pressure Careers:

• The decompression techniques he uses after each intense show
• His approach to shame work and building daily practices of self-respect
• Why "the body keeps the score" applies to performers and everyone else

Real Success Strategies:

• Why taking calculated risks is non-negotiable when following your dreams
• How to channel aggression and energy into "ferociously" pursuing your goals
• The art of reading workplace culture before making your mark
• Building relationships across different departments and industries

My Biggest takeaways:

• "I've lost if I'm worried about looking good" - Alex's philosophy completely changed how I think about authentic performance
• The game-changing difference between "eustress" (stress you choose) and reactive stress
• Why technique and safety should never be compromised for commercial success
• How to maintain your artistic soul while working within commercial systems

This episode is perfect for:

• People struggling with rejection in their careers (honestly, everyone)
• People looking for real strategies to build genuine self-worth
• Fans of The Outsiders who want to see behind the curtain

This conversation combines brutal honesty about the entertainment industry with life advice that goes way beyond theater. Whether you're chasing Broadway dreams or just trying to build resilience in your own path, Alex's insights on technique, self-worth, and staying authentic will hit you right where you need it.

I'm genuinely excited for you to hear this one. Alex brought such depth and vulnerability to our conversation, and I think his perspective on channeling energy into "ferociously" pursuing your dreams while maintaining your humanity is something we all need to hear.

Subscribe, give this episode 5 stars, and leave a review!

Follow Alex: @AlexJGSings on Instagram | Alex Joseph Grayson

Connect with me:

• Instagram: @theguyset and @guysetpodcast
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com

See you next Tuesday!

This week's episode is all about how to actually restart and build momentum again when everything feels completely scattered and you've been stuck in a cycle of bad habits.

After moving to a new apartment and completely losing my routine, I've been struggling with all the habits that used to make me feel good: going to the gym consistently, eating well, journaling, and staying off my phone before bed.

If you've ever felt like you've lost your momentum or can't seem to get back into the swing of things, this episode is for you. I share my honest experience of falling back into bad habits like scrolling until I fall asleep and snoozing my alarm 17 times, plus the overwhelming feeling of having stuff everywhere and not knowing where to start.

What I breakdown:

• Why starting over feels so much harder than you expect (even after just a few days off)
• The physical and mental reality of rebuilding routines from scratch
• 5 practical ways to start again when you're feeling stuck
• How to shift from focusing on what you didn't do to celebrating what you did
• Why consistency matters more than perfection when rebuilding habits

The 6 ways to start again:

1. Make a list of what you DID do (instead of dwelling on what you didn't)
2. Choose 2-3 things you actually want to do and will enjoy
3. Call someone - your mom, dad, friend, or whoever will make you feel connected
4. Add something completely new to try (this is your "start" moment)
5. Bring back one thing you used to love but dropped (this is your "again" moment)
6. Go outside and take a walk

Whether you're dealing with a recent move, coming out of summer mode, or just feeling generally off your game, this episode offers real talk about the struggle and actionable steps to get back to feeling like yourself. Perfect timing for anyone looking to reset as we head into fall.

Subscribe, give this episode 5 stars, and leave a review!

Connect with me:

• Instagram: @theguyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Ask me anything or email: [email protected]
• Ask Me Anything: guyset.com

See you guys next Tuesday!

I never thought a conversation with my Uber driver would completely change how I think about meeting new people. What started as a dreaded 55-minute airport ride turned into one of the most genuine conversations I've had in months and it's got me thinking about how we've lost the art of talking to strangers.

In this episode, I'm breaking down the incredible questions my Uber driver asked that turned small talk into real connection. I'll give you the exact conversation starters that work (perfect for dates, networking events, or just meeting new people), and explain why having zero expectations from a conversation can make it the most memorable one you'll have.

I'm also diving into my own antisocial tendencies, why I initially dreaded talking to this guy, how the conversation completely shifted my perspective, and what it taught me about putting myself in uncomfortable situations. Plus, I'm sharing the networking lessons I learned and why "see you down the line" might be the most honest goodbye ever.

If you've ever wondered how to have better conversations with strangers, want to improve your small talk game, or just need a reminder that real human connection still exists beyond our phones, this one's for you.

This episode is perfect for men in their 20s looking to improve dating success, social skills, conversation abilities, and networking confidence. Whether you're struggling with social anxiety, want better first date conversations, or need networking tips for career growth, this episode delivers actionable advice.

Subscribe to Guyset for weekly episodes on dating, career advice, social skills, and personal development for men in their 20s. Available on Spotify, Apple Podcasts, and YouTube.

Rate 5 stars ⭐⭐⭐⭐⭐ | Email: [email protected] | Follow @theguyset on all platforms

Connect with me:

• Instagram: @theguyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com
• Read my substack: guyset

See you next Tuesday!

I'm back with another moving story that proves I still haven't figured out how to move without everything going wrong. I'm recording this from a hotel room in LA because I had to travel for work just three days after finally getting into my new place.

I'm sharing my latest NYC apartment move experience, from co-op board approval nightmares to furniture delivery disasters that had me stressed all day. This move was supposed to be way smoother than my first NYC disaster, but somehow I still managed to mess things up in creative new ways. If you're planning a move, thinking about living alone for the first time, dealing with NYC co-op buildings, or just want to learn from my mistakes so you don't repeat them, this episode is definitely for you. I'm breaking down everything that went wrong, the lessons I learned the hard way, and giving you the real talk about what those first few nights living completely on your own actually feel like.

Moving Tips I Learned:

• How co-op board approvals actually work (and why they take forever)
• Why you should always measure your apartment before buying furniture
• Building delivery rules and elevator reservations explained
• How to handle moving company scheduling changes

Furniture Shopping Mistakes:

• What happens when you order a couch without checking return policies
• Apartment delivery time windows and building restrictions
• How to avoid buying furniture that's too big for small NYC apartments

Living Alone for the First Time - What to Expect:

• Transitioning from roommates to solo apartment living
• Building a social support system when you live alone
• Mental health tips for first-time independent living
• How to stay social and avoid loneliness in your 20s
• The weird reality of transitioning from roommates to solo apartment living
• How everything becomes your responsibility - from social plans to staying motivated
• Building a solid support system when you live alone (friends, family, places to go)
• Why you need to be comfortable with yourself before living solo
• Mental health strategies for first-time independent living
• How to stay social and avoid loneliness in your 20s without roommates
• The importance of reaching out and making effort with friendships
• Balancing alone time vs. social time when it's all up to you
• Learning to enjoy your own company and what you discover about yourself
• How to create structure and routine when there's no one else around
• Managing the emotional adjustment of total independence
• Tips for staying connected when you're the only one making the effort

Subscribe and follow for weekly advice on navigating your 20s! Give this episode 5 stars, and leave a review!

Connect with me:

• Instagram: @theguyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com
• Read my substack: guyset

When I walked out of "John Proctor is the Villain" on Broadway, I knew I wanted to have a conversation about the guys in the show and I got to have it with two of them, Gabriel Ebert and Hagen Oliveras. These guys don't play the heroes in this show, they play the guys we recognize, the ones who make us uncomfortable because we've either known them or we've been them.

Gabriel portrays Mr. Smith, a beloved teacher whose true nature becomes devastatingly clear. Hagen plays Lee, a troubled young man whose attempts to connect consistently harm the people around him. What struck me wasn't just their performances, but how these roles have forced them to confront difficult truths about masculinity that most of us would rather avoid.

In this conversation, we explore:

• How playing morally complex characters has changed their understanding of male behavior
• The moments from their own lives they've had to reckon with through these roles
• Why defensiveness and withdrawal often make men's struggles worse, not better
• The difference between struggling and how you choose to struggle
• Why vulnerability, not protection of ego, serves everyone better

Gabriel and Hagen have spent months inhabiting these characters, and their insights into the psychology of men who cause harm are both unsettling and necessary. These are the conversations that matter, the ones that might actually help us become better men. Thanks for listening and share with a friend or someone you think might resonate this one.

Subscribe, give this episode 5 stars, and leave a review!

Connect with me:

• Instagram: @theguyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com
• Read my substack: guyset

See you guys next Tuesday.

I'm recording from my first NYC apartment for the last time after three years, and I'm honestly feeling all kinds of ways about it. In this episode, I'm getting real about the complex emotions that come with moving out and the transition from roommates to living alone for the first time.

I'm sharing my most vulnerable thoughts about this change, from my catastrophic first NYC move three years ago to how I'm preparing mentally for living on my own. If you're going through something similar, I think this episode will help you feel less alone about this process.

What You'll Hear in This Episode:

My worst moving disaster story: How my movers completely disappeared (0:04:00) Essential moving tips: The red flags I missed and how to avoid the same mistakes (0:09:35) Living alone vs roommates: My honest feelings about this major transition (0:21:19) Moving anxiety advice: Why it's totally normal to feel both excited and scared (0:25:00) City moving hacks: Dealing with co-op boards, storage, and timing issues (0:11:58)

Episode Timestamps:

0:00 - Intro: Last recording from this apartment 4:00 - My nightmare first move to NYC story 9:35 - Lessons learned: How to choose reliable movers 14:14 - Managing moving stress while working full-time 18:59 - The emotional reality of leaving home 23:44 - Why it's okay to feel sad and excited at the same time 28:37 - Living alone for the first time: My expectations

Key Takeaways from This Episode: -Always read your moving contract fine print (learned this the hard way!) -Confirm moving times multiple times before moving day -Don't always choose the cheapest moving option -Habitat for Humanity pickup tip for donating furniture -How to mentally prepare for the roommate-to-solo transition -Why mixed emotions about change are completely normal

Perfect for Listeners Who Are:

-About to move out for the first time -Considering living alone vs with roommates -Dealing with moving anxiety or stress -Navigating major life transitions in their 20s -Looking for honest podcast content about growing up

Guyset is a weekly advice podcast for guys in their 20s covering relationships, career, mental health, moving, roommates, and all the life transitions nobody teaches you or talks about.

Connect with Guyset:

• Instagram: @theguyset
• TikTok: @theguyset
• Ask Me Anything: guyset.com
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Subscribe to my weekly newsletter on Substack: guyset

See you guys next Tuesday!

Should you shave before a date? Is it okay to show up to a date in work clothes? When will you finally know what you want to do with your life?

In this Ask Me Anything episode of Guyset, I pull 10 real listener questions from my Spider-Man bucket hat and deliver honest and real advice for guys navigating their twenties. From dating anxiety to career setbacks, friendship changes to quarter-life crisis fears, these are the questions you've thought about but never knew who to ask.

Timestamps:

03:28: "Should I shave before my date?"

05:41: "Is it all right to show up on a first date in work clothes?"

08:02: "Is it bad if I'm a bad texter for dating?"

12:35: "A lot of my friends are moving and I'm feeling anxious about how far apart we're all going to be. I don't know if there's any advice for this, but I'm wondering if other people are feeling this way too."

19:44: "My girlfriend and I have been together for a year. What should I get her?"

22:07: "Should I keep a condom on me?"

24:18: "My recent review at work wasn't as good as I wanted it to be. What should I do?"

29:00: "When should I feel like I know what I want to do?"

33:44: "Any tips to help me get out of a slump? I'm feeling really lazy recently."

38:05: "When do you think a girl should start paying for dates?"

What You'll Learn:

Dating & Relationships: Pre-date grooming essentials, texting etiquette that actually works for dating, and perfect one-year anniversary ideas Career Challenges: How to bounce back from bad performance reviews and turn criticism into career growth Life Transitions: Dealing with friends moving away and the anxiety of post-college life changes Personal Development: Morning routine hacks to beat laziness and build momentum Real Talk: When you should actually know what you want to do (spoiler: probably not yet)

Perfect for: Guys in their twenties dealing with dating stress, career confusion, friendship changes, or general life anxiety. Also great for anyone who wants honest perspectives on modern masculinity and relationships.

Why This Episode Hits Different: It's 10 Questions Every Guy in His 20s Is Asking (But Won't Say Out Loud). This isn't your typical self-help podcast. I'm going through the exact same struggles as my listeners – quarter-life anxiety, career uncertainty, watching friend groups scatter. My advice comes from lived experience, not a textbook.

Subscribe to Guyset for weekly conversations about what should be talked about for guys in their twenties. New episodes every Tuesday.

Submit your questions for future Dear Guyset episodes:

• DM: @theguyset
• Email: [email protected]
• Website: guyset.com

Connect with me:

• Instagram: @guysetpodcast
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com
• Read my substack: guyset

See you next Tuesday!

I used to freeze up every time my boss asked how things were going. I'd ramble about how "things are good, things are moving" without actually saying anything meaningful about my work or impact.

Recently, my boss left and I had to have THE conversation with our CEO about my role and future. I was terrified. But this time, I came prepared with a framework that completely transformed how I present myself at work.

What I cover in this episode:

• The 3-example method that helped me showcase real impact instead of just listing tasks
• How to attach concrete numbers to your accomplishments (even if you're not naturally data-driven like me)
• Why "here's what I can do for you" works better than "how can I help?"
• The cringe conversation I had a year ago vs. the confident one I just had with our CEO
• How to prepare for promotion and raise conversations without sounding entitled

Perfect for anyone who:

• Gets nervous talking to their boss about their work
• Struggles to articulate their value without feeling braggy
• Feels stuck in their current role but doesn't know how to advocate for advancement
• Wants to build confidence in high-stakes workplace conversations

I also break down Barbara Corcoran's legendary rejection letter to Mark Cuban that got her on Shark Tank - it's a masterclass in turning rejection into opportunity and showing your worth with confidence.

If you've ever felt like you're doing good work but can't seem to communicate that effectively to the people who matter, this episode will give you the tools to change that conversation.

New episodes every Tuesday with career advice and life skills for navigating your twenties.

Follow, Subscribe, give this episode 5 stars, and leave a review!

Connect with me:

• Instagram: @theguyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com
• Read my substack: guyset

See you guys next Tuesday.

My roommate Reid is back! After living together for three years in our East Village apartment, we're moving out.

This is his second time on the podcast and it's the perfect time because we're both going through some major life changes right now. Reid is moving out to live with his girlfriend and I'm going to live on my own for the first time. Reid also just finished a pretty long job search - 50+ interviews across 10+ companies over several months. After dealing with lots of rejection, he landed a great new role and learned a lot along the way. He talks about working with an interview coach, how he stopped sounding rehearsed in interviews, and his approach to salary negotiation. If you're considering a job change, Reid's experience offers some useful perspective.

We talk about his six-year relationship which has been long-distance the entire time. Reid explains what's worked for them and his advice for long-distance relationships.

Since we've been roommates for three years, I wanted Reid's thoughts on what makes roommate situations work well. We talk through the practical stuff that matters more than you'd think like cleaning habits and talking about friends coming over. We also talk about why most guys are terrible at keeping in touch with their friends.

Then Reid takes on my "Dear Guyset" segment, addressing topics like dating uncertainty, relationship disagreements, asking for a raise, and managing workplace conflicts.

What We Cover:

• Surviving a brutal job search and coming out stronger
• Long-distance relationship tips that actually work
• Roommate advice for guys in their twenties
• Moving in with your girlfriend for the first time
• Why we're all terrible at texting our friends back
• Workplace advice and career transitions

If you're navigating any major life transitions in your twenties, this one's for you.

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Connect with me:

• Instagram: @theguyset
• Instagram: @guysetpodcast
• Weekly newsletter: guyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com

See you guys next Tuesday.