Q:

Ambiguity using a Sortable List of Dates

I have a basic vertical list of dates which can each be dragged to reorder the list, with the goal being to allow the user to change the order and date of each item to their liking.
An example list of reorderable dates is:

November 2: some text here
November 2: more text here
November 3: some more text
November 4: even more text

I have noticed one use case which is proving problematic:

Dragging an item in between two dates which are the same = no problem
Dragging an item in between two dates which are different = ambiguous
Dragging an item to the start of the list = no problem
Dragging an item to the end of the list = no problem

It is this 2nd use case which is the problem: when dragging to a destination which is in between two different dates, we cannot be sure which date the user is intending to choose.
So in the above example list, I would be dragging item #4 in between items #2 and #3. As you can see, it becomes ambiguous to determine the new date for the item.
Any ideas on how to combat this problem would be much appreciated!

A:

I think the problem is conceived by the fact that you see the combination of a date and the text as 1 thing. 
Let me make a suggestion: make it look a bit more like a calendar. Quick mockup:

In this example the red squares can be dragged and there is no confusion of which date an item will get since the whole day is a "drop-zone".

