"I've even shared some personal stuff about myself, and in so doing I feel like I'm just following the assigned task, playing the game I'm supposed to be playing."

Ah, the old about game :-) You're supposed to share yourself as you are in the moment. I have brown eyes, so what or my mother died when I was 3 -- I told that to the female barber yesterday and she instantly said how sorry she was and I instantly deflected it; both of us were not in the moment; it didn't cost me anything to talk about what happened 53 years ago now I'm grown and yet I didn't take the opportunity to get "closer" to her by thanking her personally for being sorry for my loss but she didn't stop either to think about the age difference and that I was telling her, a stranger, and listen to the rest of my "story" which was about how my father took me (when I was 3 & 4) to the barber shop with him because I only have brothers and I was a little girl. . . If she had commented on the sweetness or appreciated my being a little girl out with her father after their mother/wife had died, etc. it would have been a "meaningful" moment but both of us rushed by it rather than connect with one another.