#124 - High Expectations, Loosely Held: The Mindset for Modern Dating
Oct 13, 2025
episode NOTES
We’ve all done it. One good date and suddenly you’re imagining the wedding playlist. In this episode of Guyset, I break down what I call the Ted Mosby Syndrome, when your expectations race ahead of reality and set you up for disappointment.
I talk about why so many of us build storylines around people we barely know, how that pressure kills real chemistry, and what it actually means to hold high expectations, loosely. Building on my last episode about how to approach someone at a bar, I share practical advice for handling early dating, managing expectations, and keeping your confidence intact.
The biggest mindset shift: Don’t tie your self-worth to someone else’s approval. When you stop chasing potential and start focusing on reality, dating gets easier, more fun, and a lot more honest.
If you’ve ever felt let down after a first date or caught yourself overanalyzing every text, this episode will help you approach dating with clarity, confidence, and calm.
When I sat down to record this one, it hit me how much pressure we all put on first dates. We build entire stories in our heads before the drinks even arrive. And when it doesn’t go perfectly, we spiral.
We overthink it because we want it to work. But that same pressure is what makes it fall apart, kind of like what I talked about in Getting Ghosted Hurts, But It Might Be the Best Thing That Happened to You.
“I held my expectations so high for every girl that I met in the beginning,” I said in the episode. “I kind of came with these things I wanted with each person on every date.”
That line says it all. Most of us do this without realizing it. We meet someone, feel that spark, and immediately start picturing the future, then feel crushed when it doesn’t match the fantasy.
What I realized is that it’s not about dropping expectations entirely. It’s about holding them loosely.
“It’s important to have high expectations about what this could potentially be,” I explain. “But loosely hold those high expectations.”
That small shift changed everything for me. When I stopped trying to control the outcome, I started enjoying the process, the same mindset I used when I finally got over Gym Anxiety.
This episode is the sequel to Ruin the Friendship. That one was about finding the confidence to walk up and say hi. If that one was about starting the conversation, this one is about what happens next.
