I think that “getting good” at the “free association” game is in finding the sweet spot / negotiation between full freedom of association and directing toward your own interests, probably ideally with a skew toward what the other is interested in. If you’re both “free associating” with a bias toward your own interests and an additional skew toward perceived overlap, updating on that understanding along the way, then my experience says you’ll have a good chance of chatting about something that interests you both. (I.e. finding a spot of conversation which becomes much more directed than vibey free association.) Conditional on doing something like that strategy, I find it ends up being just a question of your relative+combined ability at this and the extent of overlap (or lack thereof) in interests.
So short model is: Git gud at free association (+sussing out interests) → gradient ascend yourselves to a more substantial conversation interesting to you both.
I think that “getting good” at the “free association” game is in finding the sweet spot / negotiation between full freedom of association and directing toward your own interests, probably ideally with a skew toward what the other is interested in. If you’re both “free associating” with a bias toward your own interests and an additional skew toward perceived overlap, updating on that understanding along the way, then my experience says you’ll have a good chance of chatting about something that interests you both. (I.e. finding a spot of conversation which becomes much more directed than vibey free association.) Conditional on doing something like that strategy, I find it ends up being just a question of your relative+combined ability at this and the extent of overlap (or lack thereof) in interests.
So short model is: Git gud at free association (+sussing out interests) → gradient ascend yourselves to a more substantial conversation interesting to you both.