A technique for getting into conversation with strangers is to make one extra remark, beyond what is called for.
The remark must be short and simple and works best when it’s also positive or humorous. The content of the remark doesn’t matter as long as it’s in good taste – it simply indicates your interest in continued conversation.
Waitress: how are you?
Me: good and you?
Waitress: doing well.
*could go straight to ordering, but…
Me: cool, I came in yesterday and really liked the coffee and scone.
This is why I’ve said before to reject absolute utility in any human interaction. Charming superfluousness can be added at any time to brighten a day or make a connection.