M 30+. So, I wanted to vent and ask, how to stop losing opportunities? What I have to work (and how) on inner game?

Had a big crush with a girl at the office and I know it was mutual. Flirting was there but I also soft ignored her. Worked wonders. But as in many instances in my past, I did not push more, I procrastinated asking her out and I lost a very good chance to escalate more.

Then I went through health issues, stayed 4+ months out of office. Fast forward to March this year, I came back and noticed her different, but between my recovery and back to work, I just didn’t pay attention. Well I just learned today, September, she is pregnant.

Feels like someone else had eaten my lunch while all my health issues happened.

Heartbroken, yes

Why I procrastinated? I didn’t want to look bad at the office, I am always careful with reputation, especially working a corporate job and having a somewhat high rank. She was just a early graduate.

This was not the first time something like this happens. Throughout my professional life (that occupies most of my time) I’ve had so many opportunities like this, but this hurt the most.