Testing the waters

So me m22, want to test the waters with a close family friend since childhood F21 to see if things could go anywhere behind the scenes, she’s always been in and out of relationships that are quickies, I want to try it subtlety but not sure if it should go for a more direct route of a risky truth or dare while drinking, we get along very well when we hang out in family or friends events and even just 1 on 1 I really find her attractive and not sure how to approach it, can I get some advice on how to approach this without possibly ruining the relationship