I don’t know that you should. I know it’s been said a million times, but I feel that may be the end of the friendship as you know it. Once you cross that line you will change the nature of that relationship forever, for better or worse. Let him lead. Try putting him in situations to make him show you if he feels the way you do. Example: It’s halloween week, pick a scary movie to watch together and see if he holds you with more than a friendly touch. HA! Or, feed him that one extra drink and see if he spills his guts. Anything to get him to do it first!