If your Column.getValue returns null, you wouldn't be able to popup DatePickerCell.datePicker since you pass null to its datePicker.setValue method.
Here's my solution:
DatePickerCell<Object, Date> cell = new DatePickerCell(datetimeFormatter) {
@Override
protected void onEnterKeyDown(Context context,
Element parent,
Date value,
NativeEvent event,
ValueUpdater<Date> valueUpdater) {
if (value == null)
value = new Date();
super.onEnterKeyDown(context, parent, value, event, valueUpdater);
}
};