Somebody from your past with whom you have never slept with, until now....
Rory: Hey Chris, don't you know that girl?
Chris: Yes, she looks Familiar.
Rory: But we're out looking for Strange.
Chris: All I can find is Strangely Familiar
Rory: Guess that will have to do.
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The act of cheating on your significant other with the same person (or persons) consistently.
J-Dizzle been hittin' that Familiar Strange for a coupe of years now. Meanwhile, his baby mama back at da house gettin' her some Familiar Strange from the mailman, D-Rod.