Nowadays, I don't, but I grew up in an environment that was different. Speaking to strangers was a norm, not something that merited attention. Modern western culture is extremely anti-social these days. I would say I'm naturally reserved but my tolerance and comfort level in situations where I have to integrate my life with others is high.
My answer may not be of great help, but if you are struggling with this I would really encourage you to move to a completely different environment (i.e. Latin America) where the norms are different. In my opinion this is not something an individual can easily solve. It's a cultural issue. Culture can take a lifetime / generation to change and that's if the people collectively decide it's worth changing.
If we get real, the loneliness epidemic is something we foisted on ourselves. Striving to avoid any awkwardness or discomfort is precisely why social life is so sterile these days. You can't have your cake and eat it too.