Hi, alannuhh, and welcome to Psych Central! Since he has had this same dream over all these years and cries as a result, I think he should talk to a therapist. They help people to get over such issues. (And it does not mean that your friend has a mental illness! Folks go to therapists for all sorts of reasons.) He is still really hurting from that loss, and yes, needs to get a good night's sleep.

Thanks for being such a caring friend. If he won't go along with seeing a therapist, then tell him to go to a regular doctor and tell him/her about not being able to sleep and specifically why. Okay?