This is a classic matching problem, I believe.  Based on your description, you 
are looking for a 1-to-1 nearest-neighbor match based on the absolute 
difference in dates, with the constraint that once a subject in File 2 is used, 
all of their records are discarded.

Correct?

There are two classical approaches: greedy matching and global optimal 
matching.  While the greedy approach is simple to implement and often works, it 
can sometimes get into trouble (i.e., run out of good matches). The optimal 
approach would use the Hungarian algorithm (e.g., LSAP function in the clue 
package) to find the combination of matches that results in the lowest total 
date difference across the entire dataset.

Ravi

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