It depends. It always depends. Honestly, just be yourself. We hate fakes. HATE. Some people like fakes. Stupid people. Anyways, you don't have anything to loose. I think he would still be your friend even if he didn't want to date you. It seems as if he cares a lot. That's good. I'm not going to give you advice about how to specifically "woo" someone. You know them best. What they like, don't like. Type only has so much to do with it. You have the advice of other ISTJ males here and those that have married or dated them. Take that and run (Yes, I know it's hard. Do it anyway. Grow.). Ignore the ENFP for a second [kyuuei - ]. Just go for it. Like you might any other guy. You care about him, you are attracted to him. He, from my stand point, cares and is possibly attracted to you too. You don't have anything to lose. You have a closer friend to gain.