A little background In my childhood my father was very emotionally reserved, most likely due to some large insecurities, and was very critical and judgmental towards me. As a result, while I was growing up, I never got much practice accepting myself and always tried to make other people happy (primarily my father but also any other males in my life). This then spread to nearly everyone I came into contact with. I feel as though that critical period of emotional and empathic development was not taken advantage of in the slightest.

Anyway,

Now I'm a 20 year old M attending university currently going through a period of huge inner change. Trying to become more confident through focusing more on myself and my happiness and things are definitely improving, yadda yadda. I have been trying to talk to more people in general, but have been especially interested in meeting women to date and men to make meaningful friendships. However, lately I'm running into a total roadblock when trying to make meaningful connections with other people (as I understand, this is something the seddit community is always keen on improving).

I've had lots of practice with deep conversation topics, being an introvert and sort of hating the more arbitrary conversation. But in conversation, both small-talk and the more meaningful stuff, it always comes off as a more interview-style experience to both myself and the other person where I just grill them with questions in hopes that they'll share some details about themselves and best-case-scenario want to know about me as well.

To my dismay, people don't typically enjoy getting grilled. Especially when I seem too preoccupied with thinking of things to converse about next and not really living in the moment and expressing what comes naturally. Every time I've experimented with emotional expression in the past I always seem to oversell it and become that guy who gets overly excited about everything and appears annoying and fake.

I feel as though part of the problem is that I don't have a complete understanding of what makes me tick.

So what do you guys think is the best way to get to know yourself? And what are some appropriate techniques for emotional expression? Any feedback is welcome.