How to handle nulls when using Java collection sort

Naturally, it’s your choice. Whatever logic you write, it will define sorting rules. So ‘should’ isn’t really the right word here.

If you want null to appear before any other element, something like this could do

public int compare(MyBean o1, MyBean o2) {
    if (o1.getDate() == null) {
        return (o2.getDate() == null) ? 0 : -1;
    }
    if (o2.getDate() == null) {
        return 1;
    }
    return o2.getDate().compareTo(o1.getDate());
}