I have not deliberately paired two cigars but have many times smoked two in a row or at least within a few hours of each other. Usually because I was dissatisfied with the first or if is a weekend I smoke 2 or 3 in a day.
Anyway, to address your question, I think some thoughts and planning on pairing is a good idea. Personnally I would choose a Connecticut or other natural for the first followed with a medium to full Corojo or Brazil. I would always go from mild/medium to medium/full.
Of course if your first choice was a dud, let's say a Manolete, then almost anything would taste good afterward.
While it's not exactly pairing, on a weeked I will usually choose a milder smoke for mornings and something with a little body for afternoons or evenings.
I'll leave brand specific pairing to the pros.
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