I would recommend that your friend try to find you a box of "San Cristobal de La Habana" I am currently in love with these cigars. They're a 7 x 48, and have a really cool complexity. I was turned on to them about 2 months ago. You won't find them rated anywhere, which is amazing. These things are a long smoke, with a constantly changing taste. The first half will remind you of a typical Montecristo, but the last half will literally knock you down with flavor (jeez, now I'd better go light one up, my mouth is watering). Saint Luis Rey would be a good choice as well or a Diplomatico. You can never go wrong with a Romeo y Julieta or Montecristo, however I will give you my two cents on those...as a regular smoker of Cubans (I live 2 blocks from a store) you have to be a pretty impressive taster to really know the difference between a Cuban Romeo/Montecristo and one bought locally. There really isn't that much difference...therefore my recommendation would be to go with something a little more Cuban "specific" as I decribed above. Perhaps a better choice would be to have your friend pick you up a variety box with several different brands? Then you can get a true taste of Cubans. Good luck.