

What Should You Text Before A Date?
Not sure what to text before a date? Here’s exactly what to send, when to send it, and how to set the tone without overthinking.

How to Tell If a First Date Went Well
The signs to look for when you’re unsure how the night actually went

Is It Okay to Go Home With Someone After the Bar?
What it means to go home with someone after the bar, and how to decide if it’s the right choice for you

How Do You Know If You Actually Want a Relationship?
How to know if you actually want a relationship or just feel pressure to be in one

Is It Better to Focus on Your Career or Dating in Your 20s?
How to Balance Ambition, Relationships, and Timing in Your 20s

How Do You Stop Feeling Overwhelmed at Work? (What Actually Helps in the Moment)
How to regain control when you feel overwhelmed at work and everything feels urgent

When Should You Leave Your First Job?
How to know it’s time to leave your first job and the signs you’ve stopped growing

How Many Drinks Should You Have at a Work Happy Hour?
A simple rule for balancing socializing with coworkers without hurting your professional reputation.

How To Stop Feeling Overwhelmed All the Time
The real reasons your brain feels overloaded and why it’s not a personal failure

What to Do When You Feel Overwhelmed and Stressed Right Now
A practical guide for when everything feels like too much and you don’t know where to start

The Internal Monologue of Lifting
Why going to the gym feels so mental, why you overthink everything, and how to stop feeling watched and out of place

Why Do I Feel Behind Compared to My Friends?
How to stop feeling behind in life compared to your friends and feel confident in your own timeline

Why Does Life Feel Boring After College?
What Changes After Graduation and Why Adulthood Feels Quieter Than You Expected

Is It Bad To Live At Home After College?
How to Know If Staying Home Is a Smart Reset or Holding You Back

What Should Guys Wear Going Out? (Simple Outfit Ideas That Always Work)
A practical, real-world guide featuring insights from Ryan Winter on outfits, confidence, and what actually looks good.

How Do You Stay In Touch With Friends In Your 20s?
Simple ways to stay connected with friends in your 20s without overthinking or letting time pass
Conversations about dating, confidence, work, and figuring life out as it’s happening.
Editor's note
I started Guyset because nothing I was reading actually helped when I needed it. Nothing felt like it was talking to me.
So I built the thing I was looking for.
A place for the conversations you have late at night, in your head, or right after something doesn’t go the way you hoped it would.
A reminder that you’re not the only one thinking these things.
— Josh
Editor's picks

Career
Is It Better to Focus on Your Career or Dating in Your 20s?
How to Balance Ambition, Relationships, and Timing in Your 20s

Lifestyle
Why Does Life Feel Boring After College?
What Changes After Graduation and Why Adulthood Feels Quieter Than You Expected

Dating
How to Tell If a First Date Went Well
The signs to look for when you’re unsure how the night actually went








