Have Relationship Questions? Ask a Counselor for Answers ASAP
The speculations of what this may be is - 1/he has some sort of anxiety/OCD, 2/Dependent personality disorder, 3/had made a habit out of this/does not want to be bothered making choices himself.
Try to continue to set some limits with him, it may help to ignore him at times or ask him to come up with the answer himself.
Emotional Vampires: Dealing With People Who Drain You Dry by Albert J. Bernstein (Paperback - Mar. 22, 2002)