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At first this looks simple but on inspection it is an interesting problem. I feel there is not enough info yet.
To clarify you have two files, each with a title and data column
There may be one or more title values and each may be duplicated one or more times in both files
The data values...will they be unique across a title value or could they be duplicated within a given Title value?
And if I understand correctly from the first solution offered you only want the first occurrence of a title in file 1 matched to the first title of same value in file 2 and then they are not to be matched to any other.
If I am correct in the latter then a Sort followed by a Multi-Row tool can be used to create a record ID within the scope of a title value and then used in the Join in addition to the Title value to insure you only use a record once from each file in the matching.
I have provided an expanded sample data file plus workflow.