I think that agonizing over choices generally represents an attempt to internally simulate the outcome, which is uncertain. This is true for both the restaurant example (I visualize myself eating the hotdog. Does that seem pleasurable?), and the college (I visualize myself with the degree, possibly working in the field). If utility is high enough but uncertainty is still high, then it makes sense to continue simulating possible branches and weighing them in. Though I agree that at that point a well-structured way of doing that is preferable.