I went through a phase where I forced myself to socialise a lot to overcome social awkwardness and anxiety. Was well worth it, both in terms of leveling up my social skills but also in terms of eventually becoming very comfortable with myself.
The main ingredient, at least for me, was being determined enough to push through the discomfort. A lot of the early interactions were awkward, sometimes overtly uncomfortable, but that's an unavoidable part of the learning process (and I took a key lesson from it - it's okay to look like a dork, usually it's only our inner critic that turns it into an immortal sin).
Nowadays I feel a pang of sympathy when I see someone feeling shy or speaking in self-deprecating terms. I remember how that felt, and I remember how easy it would have been to have stayed inside that box for the rest of my life.
Glad I didn't.
I am still at the awkward early interaction stage.
How do you know what to say?, usually I can start the conversation but I don’t know where to take it after. How are you able to shift to the next stage when you have both agreed that the weather today is nice.
How do you get over the feeling that you are wasting their time?
Finally, how do you end the conversation when you're still going in the same direction or waiting at the same place?