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Taste is a very fickle mistress, and not all people taste things in quite the same way. A crucially important lesson is that that taste is subjective. Indeed, not only is taste subjective, but studies have shown that knowing the price of something can affect your real enjoyment of it... and there is also the "ignorance is bliss effect" to consider as well. Here are a few things that I find contribute to the taste and enjoyment of cigars:
Mood -- I've found that my mood affects my enjoyment and taste of cigars more than I would have expected. I can smoke the same cigar one day, and love it, then smoke it again when I'm in a funk and it does nothing for me. Remember, studies have found that taste is linked closely to brain chemicals which control our moods... so this makes quite a bit of sense.
Don't underestimate how much your mood can affect whether you enjoy the taste of a cigar or not.
Expectations -- People underestimate the power of expectation, which is why blind taste tests are so incredibly important in finding out what cigars you really enjoy. If you're handed an aged, rare cigar, I think two things come into play. First, you have the expectation that you're going to enjoy the cigar (or at least should enjoy the cigar).
But perhaps more important is that if you know you've been given a "special" cigar, you will pay more attention to the cigar. Knowing the cigar is something special, you'll slow things down, and look for the flavors and nuances it conveys as you smoke it.
Environment -- Just as expectations often cause you to slow down and pay attention to the flavors a fine cigar has to offer you, so does the environment you smoke it in. If you're mowing the lawn or playing poker, you're likely distracted and won't be paying much attention to what the cigar has to offer you.
However if you're sitting back, relaxing, and are able to really focus on what the cigar has to offer you, that's another story entirely. Really tasting a cigar takes time and focus; the tastes are there regardless, but like many things in life, you have to be looking to find them.
Pairings -- What you eat and drink while you smoke a cigar affects your overall enjoyment and taste drawn from the cigar. A very strong drink can overpower the flavor of subtle cigars just as easily as a bold red wine can overpower subtly flavored foods. What you've eaten or had to drink prior to smoking a cigar can also have an effect; you have only one set of taste buds, and they are a continuous system.
Age of the cigar -- Properly stored, cigars made of premium tobacco will become more refined with age as the tobaccos that compose it marry harmoniously, and rough edges in the taste become smoothed out. Often subtle nuances or "complex" tastes in a cigar can be obscured by overpowering tastes when the cigar is young.
How long to age a cigar depends on the cigar blend, as well as your personal tastes. In general, a bolder blend has more long-term aging potential, but all cigars will eventually peak at a certain point in time. When that peak hits its sweet spot depends not just on the tobacco, but more importantly on what type of taste you enjoy.
Health -- The sense of taste is closely linked to the sense of smell. Obviously, then, if you're congested because of illness or suffering from allergies, you're not going to taste a whole lot in the cigar. Body and mind are interrelated, so poor health also affects your mental state, which will change how you perceive the cigar as noted above.
The tobacco blend -- It may seem strange to some people that I've listed the actual tobacco blend last (though it is certainly not least). The reason is that regardless of the tobacco blend, all of the aforementioned factors affect the taste of your cigar as you perceive it, and perception is everything. You could have a premium aged cigar handed to you with the band taken off, and smoke it while in a bad mood during a busy activity, and you'll likely get nothing out of it.
Clearly however, just as the ingredients in your favorite meal matter, so does the tobacco blend. More interestingly, despite the best efforts of cigar makers, cigar blends vary in taste somewhat from cigar to cigar, even from the same production year. Year over year, the variance is more prominent. Still, there is a distinctive taste profile to each cigar blend, some of which you'll like, some of which you won't.
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There are other factors as well, but these are the ones that I've found to be most prominent when it comes to enjoying a fine cigar. Also bear in mind that variety is the spice of life; even if your favorite meal is steak, eating it every day will make you tire of it quickly. The same applies to cigars, so vary what you smoke to keep things fresh.
Taste is a very, very slippery thing. Time and time again, experts have been confounded when it comes to blind taste testing of anything... water, wine, beer, cigars... so there's no reason to feel bad at all. We all think we're better at it than we really are, myself included. Check some of these links out: The Subjectivity of Wine
"Expert" wine tasting: Round #1 -- Round #2 -- Round #3
"Expert" water tasting: Round #1 -- Round #2 -- Round #3
Tap water from municipal water supplies keeps winning in blind taste tests, yet people are paying $3 a bottle for Evian... there's definitely a logical disconnect there. People are buying by brand or label, not their taste buds. I like the statement from the last "water" article: In the final analysis, the price is all that separates them
When it comes to taste, the most important organ in your body is your brain, and the preconceptions it carries along with it. Your tongue and nose are mere appendages.
