> Like if I can pull up something from the last convo that'd help.
I can relate to this. Every time I'm alone with someone, my brain goes to overdrive and I ask myself questions like "what can we talk about" , "what common interests do we have", "how can I make him/her laugh", "what about this person that I don't know yet that I can ask" just to 'develop' the relationship.
But after a while of doing this, and observing myself doing this, I get burnt out and go 'f it, who cares'. If I cared about this person, it wouldn't feel such a grind to create/maintain this relationship.