However his 'pleasing you by giving me what I wanna hear' is perhaps the first part of the process, because it means he thinks you are worth making the effort to become acceptable to. If you are lucky he may progress on to being more forthcoming - or not. There are things you can do like modeling it for him by sharing some of your own struggles and shortcomings, but ultimately you've got to let him set the pace. And don't overburden him - one of the errors I've made with YFs is to forget they are children and see only the adult part of their personality. However the fact that you are 'not really allowed to hang out with him' means that there is a worrying tension at the heart of your relationship between his loyalty to his parents and his relationship with you. Beware!