Hard one. What about giving him three choices so he has to think about what he thinks is best thing to do. Or give him leading questions. How are you getting home from Xs. I dunno. That doesn't make him think. Ask - what ways are there to come home from Xs. He could say dunno. You say bus , walk , taxi. Then expand - where's the nearest bus stop How fat do you recon itd take to walk back. Give him to ring taxi firm for quote. Etc. That way your teaching him how to problem solve.