My big issue is being interested after approaching. Interested in what she has to say, I mean. I can engage in conversation and follow the threads, but for the life of me I just don't care about 90% of what people have to say in social settings. This isn't just women I want to get with, it's just that in general I really don't care about the minutiae of another person's life because it's irrelevant.

I realise that I'm an asshole and I do want to change, I don't talk to people intending to deliberately find them boring or anything like that, but jesus christ they are. I'm sure I'm just as boring to most people, I just don't know how to start down the path to be one of those people who get super engaged by everything others have to say to them. How does one drum up that level of interest?