#123 - Ruin The Friendship

Inspired by Taylor Swift’s “Ruin the Friendship,” this solo Guyset episode explores what really happens when you take the risk, from walking up to a girl at a bar to telling a friend how you actually feel. I share why I think confidence always beats regret.

Episode Summary

There’s a split second before you decide to say something, when your brain screams, “don’t do it” but your gut says, “you’ll regret it if you don’t.” That’s where this episode lives.

In “Ruin The Friendship,” I talk about the moments that change everything: walking up to a girl at a bar, telling someone you like them, risking the comfort of what’s easy for the chance at something real.

I share how this mindset shift came from a simple Taylor Swift lyric: “My advice is to always ruin the friendship. Better that than to regret it for all time.” It’s about confidence, rejection, and why most of us overthink the smallest, scariest moments of connection.

This episode is built around a three-part framework that I’ve actually used and seen work for approaching anyone new:

1. Compliment or introduction.

2. Question.

3. Confidence.

And beyond that, it’s about mindset. Because whether it’s a girl at a bar or a friend you’ve caught feelings for, the hardest part isn’t what to say, it’s deciding you’re worth saying it.

Explore More from This Episode

Feature Article: How To Talk To Girls At A Bar (Without Being Awkward)
7 Lessons: What “Ruin The Friendship” Taught Me About Confidence and Regret
Practical Q&A: Q&A: How to Talk to a Girl at a Bar Without Feeling Awkward

Notes from Josh

I recorded this one after having the same conversation with a friend recently. It was the “I want to talk to her, but I know I won’t” spiral we all fall into. If that’s you, this episode is your sign to go for it. You either know, or you never know.