Re: wedding suggestions
The easy answer would be, pick something with a reputation for lots of aging potential.
Unfortunately, I have found that there is no guarantee any particular box will age well. The best thing you can do is to smoke one fresh. If it's not at least 'pretty good', it is not as likely to blow you away in 10 years. Sell the box and try another.
Also, I think we are all a little susceptible to psychological bias. If you buy an extra special cigar, like a cab of Sir Winstons or something similar, you will be more likely to enjoy it, because we all project a little bit of our expectations onto a cigar for which we have a preconceived opinion.
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