I use to be a very shy person before my illness. I dreaded social situations like bbq's and dates but I still forced myself to them, but doing so meant I had to be prepared or I'd never have the confidence to follow through.

To prepare for a date or a bbq I would list current events, funny things that have happened at work, new recipes, and ready made intros if someone asked me who I was. One thing I learned over the years is that people love to talk about themselves. Be a careful listener and try to penetrate what most moves them.

A simple question I like to ask is "What's good in life?" first because it brings up positives in life and second because it might trigger a passion they have been working on.

I recommend keeping in the loop about current events, always having a book to read, ask, ask, ask for recipes!!! and follow something intellectual. The more mental friction you have the more ideas will pop into your head.