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I'm new to cigars as well, but have fallen in love with La Perla Habana Black Pearl Rojo Toros. So far it is a consistent smoke for me, but I also love the Padron X000.
I like Rogue Chocolate Stout and a Kristoff Maduro, the Chocolate tones do well with the cigar. I also like the Black Pearl Rojos with a Victory at Sea Imperial Porter from Ballast Point.
I like dark beers though so YMMV.