After doing around 2 dozen cold approaches, I've confirmed a pretty obvious fact about conversations: mundane topics don't get me very far and that moving beyond small talk leads to much more enjoyable approaches.

A lot of my social anxiety stems from the question: "what should I talk about with said person?" Even with my friends sometimes I feel stumped. For certain approaches, I am too generic and don't really distinguish my true self because I don't know how to move past the small talk. It's therefore no surprise that I might not get a number or text back because I haven't build the necessary connection.

Anyway, i am looking for advice on how to "deep dive" and have better conversations that don't simply include small talk. Any personal suggestions are much appreciated!