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All Episodes

Why Am I So Nervous To Ask Someone Out In Person?

Dec 23, 2025

The Dating Questions Guys Are Afraid To Ask Out Loud

Dec 16, 2025

Is It Bad To Be Jealous of My Friends?

Dec 10, 2025

How To Feel Confident In Any Room

Dec 2, 2025

What To Do When You Feel Stuck

Nov 24, 2025

Getting Ghosted, First Texts, and Rescheduling Dates: Dear Guyset

Nov 18, 2025

How To Introduce Yourself

Nov 11, 2025

When Is It Time To Start Over?

Nov 4, 2025

What No One Tells You About Job Interviews

Oct 28, 2025

The Secret Life of Walter Mitty
The Secret Life of Walter Mitty
The Secret Life of Walter Mitty

Why Do I Feel Lost In My Career?

Oct 21, 2025

High Expectations, Loosely Held: Mindset For Modern Dating

Oct 13, 2025

Ruin The Friendship

Oct 7, 2025

Overcoming Gym Imposter Syndrome

Sep 30, 2025

Finding Balance at the Highest Level with Zach Svajda

Sep 23, 2025

First Texts, Falling Fast, and the Little Things: Dear Guyset

Sep 16, 2025

The Rule of Thirds For Your 20s

Sep 14, 2025

What It Really Takes To Perform at a High Level with Alex Joseph Grayson

Sep 2, 2025

How To Start Again (And Rebuild Your Routine)

Aug 29, 2025

The Art of Talking to Strangers

Aug 19, 2025

Learning To Live On Your Own

Aug 12, 2025

The Conversations Men Avoid with Gabriel Ebert & Hagen Oliveras

Aug 5, 2025

Movin' Out (Josh's Song)

Jul 29, 2025

First Dates, Friendships Changing, and Feeling Stuck: Dear Guyset

Jul 22, 2025

How To Advocate for Yourself at Work

Jul 15, 2025

The End of an Era with Reid Becker

Jul 8, 2025

When The Door Cracks Open

Jul 1, 2025

Turning Privilege Into Purpose with Phoebe Gates

Jun 24, 2025

Dating Dilemmas, Slumps, and Mixed Signals: Dear Guyset

Jun 17, 2025

How To Find Your Style with Simon Goldman

Jun 10, 2025

The What's Next Anxiety

Jun 3, 2025

Inside the Mind of a Neurosurgeon with Dr. Randy D’Amico

May 27, 2025

What No One Tells You About Life After College

May 20, 2025

How To Write Your Story with Robert Bailey

May 13, 2025

Dancing Through Life with Jordan Litz

May 7, 2025

And We're Just Getting Started

Apr 29, 2025

What’s In Style with Taylor Reed

Apr 27, 2025

A Story of Survival with Ralph Rehbock

Apr 22, 2025

The Ego of Weightlifting

Apr 15, 2025

Learning To Live Without with Jack Ciapciak

Apr 8, 2025

Girlfriends, Hair Loss, and Gym Flirting: Dear Guyset

Apr 1, 2025

Why Guys Don’t Talk (and How to Start)

Mar 18, 2025

The Starting Line

Mar 11, 2025

How To Be More Confident When You Speak with Megan Grano

Mar 4, 2025

Overthinking, Coworker Drama, and Confidence Issues: Dear Guyset

Feb 25, 2025

How To Get Your Money Together in Your 20s with Michael LaCivita CFP

Feb 18, 2025

What To Do On Valentine’s Day

Feb 11, 2025

How To Find Real Advice for Guys in Their 20s

Feb 4, 2025

How Ordinary People Do Extraordinary Things

Jan 28, 2025

Leaving Your First Job with Luca Milletti

Jan 21, 2025

First Dates, Kissing Anxiety, and The Talking Stage: Dear Guyset

Jan 14, 2025

Introducing Me and Why I Started Guyset

Jan 7, 2025

24 Things I Learned In 2024

Dec 31, 2024

What a Difference a Year Can Make

Dec 31, 2024

The End of Year Resume

Dec 24, 2024

What Good Will Hunting Taught Me About Being a Guy

Dec 17, 2024

What No One Tells You About Living on Your Own

Dec 10, 2024

What to Buy for Her

Nov 24, 2024

How To Dress for Dates, Going Out, and Work

Nov 17, 2024

What a 61-Year-Old Wants Guys in Their 20s To Know with Martino

Nov 12, 2024

Growing Up, Getting Confident, and Living for Yourself: Dear Guyset

Nov 4, 2024

How To Plan the Perfect Date Night

Oct 29, 2024

How to Make Friends In A New City with Adam Graff

Oct 24, 2024

Life-Changing Advice for Your 20s with Robert Dugoni

Oct 22, 2024

The Things Successful People Do

Oct 15, 2024

Don’t Let Your Passion Burn Out

Oct 8, 2024

What No One Tells You About Work Trips

Oct 1, 2024

Why Do Guys Feel So Insecure?

Sep 24, 2024

Why Do I Get Scared to Commit?

Sep 24, 2024

What It Takes To Rebuild Your Life with Griff O’Brien

Sep 10, 2024

Why Not You?

Sep 3, 2024

What I Wish I Knew in College

Aug 27, 2024

What No One Tells You About Freshman Year

Aug 20, 2024

The Mental Health Conversation Guys Never Have with Gabe Finnell

Aug 13, 2024

Why You Feel Like an Imposter (And How To Change it)

Aug 6, 2024

The Mindset Shift That Can Change Your 20s with Kane Kallaway

Jul 30, 2024

How To Get Your Screen Time Under Control

Jul 23, 2024

What I Learned from Managing My First Intern with Nina Christophilis

Jul 16, 2024

Hold Your Own Opinion Higher

Jul 9, 2024

How To Have a Great First Date

Jul 2, 2024

Why Do I Get Anxiety Out of Nowhere?

Jun 25, 2024

Why Do I Talk to Myself Like This?

Jun 18, 2024

The Truth About Taking a Different Path with Zeke Bronfman

Jun 11, 2024

Why Do I Feel So Lost in My 20s?

Jun 4, 2024

The Hardest Parts of Your 20s (That No One Talks About)

May 28, 2024

Enjoy the Little Things

May 21, 2024

Write Your Own Story

May 14, 2024

Don’t Get Stuck on What Could’ve Been

May 7, 2024

How To Get a Job in Your 20s

Apr 30, 2024

Changing Your Relationship With Drinking with Brian Buzgo

Apr 23, 2024

How To Spend Time Alone (And Actually Like It)

Apr 16, 2024

Rejection, Feeling Boring, and Smelling Bad: Dear Guyset

Apr 9, 2024

Where To Start With Your Money in Your 20s with Brian Matthews

Apr 2, 2024

The Great Scattering

Mar 26, 2024

Insecurities, Approachability, and Confidence: Dear Guyset

Mar 19, 2024

The Mid-Year Reset

Mar 12, 2024

How To Survive Your First Work Trip

Mar 5, 2024

What If I’m Not Good Enough

Feb 27, 2024

Why Do I Compare Myself to My Friends?

Feb 20, 2024

Getting Canceled On, Flirty Coworkers, and Hinge Disasters: Dear Guyset

Feb 13, 2024

How To Survive Valentine’s Day

Feb 6, 2024

How To Build a Great Career in Your 20s with CEO Of Barstool Sports

Jan 30, 2024

The Dating Mistakes I Made This Year

Jan 23, 2024

Why Am I So Insecure About My Skin?

Jan 16, 2024

How To Stay In Touch With Friends

Jan 9, 2024

How To Handle the First Day at Your New Job

Jan 2, 2024

Why Does New Year’s Feel So Overwhelming?

Dec 26, 2023

Texting Rules, Hookup Timing, and Tipping Etiquette: Dear Guyset

Dec 19, 2023

What No One Tells You About Leaving Your Job

Dec 12, 2023

How To Make the Holidays Less Stressful

Dec 5, 2023

What I Learned About Myself at My High School Reunion

Nov 28, 2023

What It Really Takes To Start Something From Nothing

Nov 21, 2023

Dating Questions, Loneliness, and Seasonal Depression: Dear Guyset

Nov 13, 2023

What 23 Taught Me

Nov 7, 2023

The Highs and Lows of Your 20s with Ryan Heaton and Marathons with Ryan Heaton

Oct 31, 2023

The Truth About Dating in Your 20s with Luke Lenny

Oct 18, 2023

Figuring Out Life After College with Luke Lenny

Oct 17, 2023

Pickup Lines, Ex Photos, and Work Happy Hours: Dear Guyset

Oct 10, 2023

How To Build Gym Confidence

Oct 3, 2023

How To Talk to Girls at a Bar

Sep 23, 2023

How To Be a Good Roommate with Reid Becker

Sep 19, 2023

How To End A First Date Respectfully

Sep 12, 2023

The Body Image Conversation Men Never Have with Ryan Winter

Sep 5, 2023

How To Fix Your Sleep Schedule

Aug 29, 2023

What Every Guy in His 20s Should Know About Money with Jack Farley

Aug 22, 2023

Why Do I Get Overwhelmed So Easily?

Aug 15, 2023

The Realities of Moving Home After College with Patrick Kelly

Aug 8, 2023

Why Do I Struggle To Talk About My Feelings?

Aug 4, 2023

How To Build a Career You Actually Want with Ben Birnbaum

Jul 28, 2023

First Date Tips for Guys (What to Do Before, During, and After)

Jul 21, 2023

How To Travel Smarter with Zach Griff

Jul 14, 2023

Why Do I Take Ghosting So Personally?

Jul 7, 2023

Inside New York’s Wildest Restaurant Stories with Michael Cecchi-Azzolina

Jun 30, 2023

How To Be Good at Your First Job

Jun 30, 2023

Why I Started Guyset

Jun 23, 2023