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For a while my go-to move after leaving a restaurant with a date was to say something to make us both laugh, and then put an arm around them and squeeze a bit in a friendly way.
If they lean into it, keep the arm there, physical contact makes it much easier to flirt.
If they don't lean into it, just let go and drop it for now. It's easy enough to brush off as a friendly gesture.
I also found that it's generally very sexy to actively make it easy for the other to say no. The easier they feel it is to just shut things down, the easier it is for them to keep exploring where things might go.