> Does it get easier over time for you?

Not OP, but wanted add for myself it did.

I took the CBT approach. First to change how I thought about things (as a skill to practice) and then that allowed me to do a form of exposure therapy. Mostly finding something small to start with, a single relevant question or comment that is genuine. Saying something nice to someone, like a stressed out cashier at the grocery store goes a long way, or commenting on something like someone reading the packaging of a item and you know it and can give a brief review.

I didn't start trying to have deep conversations or expectations of ever seeing that person again. Only simple interaction for social skill improvement and over time this small talk started to come more naturally. Then that snowball into this lighter feeling around people (so anything would have been perceived as rejection before became not personal and moved on) and that, in gaming terms, was a level-up to more meaningful interaction, then another level-up and another etc. This is a decades long practice that is still going. Like many skills some pick up faster than others.