The Cigar Conundrum?

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Cuban Reloba. Like CanuckSARTech said in the funny response, why didn't they bring anything awesome? Plus these are pretty hard to buy anywhere besides Cuba. The down side is you'd have to smoke it too.

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If he's a really dear friend and understands cigars, I'd go for a cigar that has "inherent" value in a sense, rather than just a blatantly expensive cigar; as I agree with what some posts have mentioned regarding the showing off factor.

Personally, It'd be a pleasure to offer some of my RA 898s or aged Cohiba or Monte Especiales.

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When smoking with a seasoned buddy, I like to smoke either something that he really likes that I'm not as familiar with, or vise versa. That way he can describe what he likes about the cigar while I am also smoking it, and get more insight into his tastes. And then every time I smoke that cigar thereafter I'll say a prayer for that buddy.

In this scenario I would grab us something that I really like. In an after-dinner, post-steak scenario (assuming we have a decent amount of time), I'm thinking either a Liga Privada T52 or a Padron Anniversary (probably 45th or '26 #9). If I'm feeling like it's a Cuban night, then a Party 898v or SP2 (I find Partagas seems to go great post-steak), or maybe an RA Extra. Then I can talk about why I like that stick and see what his take is.

--Obviously if Piggy came over I'd give him some random RE, lol.

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I'd offer whatever is smoking good at that time ( if I still have two ) otherwise I would open a new box, so it will be new for both.

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