So the 3rd one wanted me to try harder, but my issue is mainly that I'm trying to hard?

I get what you're saying tho. Standard 'how was your weekend' responses just seem like such nothing burgers. She knows I don't care, I know she doesn't care, why are we discussing it? I'm trying (unsuccesfully) to create bits/banter. I find that makes for more compelling conversation that tells you more about who you're talking it. Could I just try doing what I'm doing now but in a more concise way and doing my best to keep things playful?

I find the point about 'lack of confidence' interesting. To be honest I do think I try and avoid boldness in my OLD interactions as to avoid exposing myself to rejection/rebuff. Are you saying im hamstringing myself by doing that?