One of the best pieces of advice I can give, something that has helped me start talking more with strangers, is this:

When I’m speaking to someone in a service role, like a waiter, a cashier, or a salesperson, I remind myself that I’m just one of hundreds of people they interact with that day. To them, I’m simply another brief interaction. So if I say something awkward or if the conversation doesn’t flow perfectly, it’s not a big deal. It’s probably just one small, forgettable moment in a long series of conversations they will have that day.

Thinking about it that way helps me relax and not put so much pressure on myself. At the same time, some of the most meaningful or unexpected opportunities can come from simple conversations with strangers. You never really know what a small interaction might lead to, whether it is a new connection, a new perspective, or even an open door you did not see before.

One tip for the introverts out there:

When the service worker and you do the back and forth of "How are you doing today" - "Fine, you?" - "Fine"

Yeah don't do that, try out this phrase "It's my Monday" [0] instead of "Fine, you?"

You'll typically have them telling you what day of their work week they are in which is not usually the actual day of the week! Because managers schedule people in service positions in wacky ways.

That little bit of human connection around labor and work, man it does wonders. They know you know what it's like, that you see them as a person, and you care a little bit. Really gets the conversation going if there isn't too much of a line.

[0] Use any day of the week, but do use a weekday. Monday or Friday works best though.