Pre-university, I worked in tech support at a dot-com startup. I was extremely shy and just calling hardware vendors caused me anxiety. During university, I worked at a games shop where I slowly opened up by interacting with the customers. I remained very shy with women but ended up meeting a girl there. When things ended 10 years later, I was shocked to find that I was still having difficulties in that respect.

I sought a book to help and picked up Models by Mark Manson, a book about dating, and it completely altered my perspective in many ways. I realized that I wasn't shy per-se: I was needy. In my desire to please (not only women), I was, fundamentally, dishonest to others and myself. I had some work to do.

My path to a "good place" involved following the advice in the book: Focus on yourself, and develop interests. I started working out, joined a book club, went on hikes... some things stuck, others didn't. I didn't do any of these things to please anyone, but for myself. (Atomic Habits is a great book in this respect)

I also kept on reading and found Stoicism as a guiding philosophy of life. I started with Manson's popular "The subtle art of not giving a f*ck" and Ryan Holiday's "The Obstacle is the Way", and soon progressed to the texts of Marcus Aurelius, Seneca, and Epictetus.

I still feel awkward at times but by journaling and keeping lessons from philosophy present (e.g. via Readwise), I reflect and let go of it.

I hope some of the above helps :)