WOW, you known him best and so you will have to use your own judgment just how to make the approach…”Chaim you haven’t mentioned whether you have found a job or a dorm yet. I just want you to know that if you would like my help doing research for either just let me know and I will do my best to assist”
Or you might want to go a different way. “Chaim, I haven’t heard anything from you in regard to either a dorm or a job.. Are you having trouble deciding what you want to do?” Whichever way you choose, be calm and speak in a very non confrontational manner.