Not a failure if the experience that accompanied it was amazing.
A $400 cigar that is not very good, would make an amazing experience turn miserable because
I just got hosed on $400. Let's look at your situational examples from the point of view that you just realized the $400 cigar is a complete dud.
A wedding of s family member or close friend.
First of all, everyone is complaining about the cigar smoke so, that's super annoying. Then they get weird around me because of my pretentious response of, "Hey, I'm outside and can smoke where I want. Besides, this is a $400 cigar!" and I start ruining the overall experience for everyone. Then, the moment I realize this is a crappy cigar and nowhere near worth $400, I chuck it with a fit of rage. ...wait, what's that smell? Ah crap, the grass is on fire because of that cigar now. Chaos ensues. Not a great moment.
"Doc, can you hold this $400 cigar for me while I cut the umbilical cord?" I don't see that going over very well. Later, you are at home thinking about how much that $400 cigar didn't live up to the hype and you literally burned $400. Anger begins to set in but you remember, you are a new father. You go in to play with your child and they end up throwing up and crapping at the same time. Blah.
Standing in front of an amazing waterfall.
And you keep having burn issues because there is too much humidity in the air. Then you start wondering if the cigar was crap to begin with or if you ruined the cigar by choosing to smoke it in such conditions. That snowballs into how your wife is right about you not being able to do anything correctly and all you do is burn the family money on cigars which jogs her memory of how you set your sister's wedding on fire and you refuse to change the baby's diaper or deal with spit up. You jump off the waterfall to end it all but you end up living to see another day because the water broke your fall. Embarrassing and not a great moment.
This is a great feeling. I love closing major deals. But if I light up a $400 cigar and it sucks, all I'm thinking about is how many more major deals I need to close to justify smoking a crappy $400 cigar. Inevitably, the wife is yelling because she saw the bank record where you spent $400 (+tax) at the local B&M. She comes out yelling because you don't need another humidor and you tell her, "Babe, I didn't buy another humidor. I bought a cigar." "
A cigar!?!" she screams!! "I HOPE IT WAS THE BEST MOMENT OF YOUR LIFE!" ...and all you can do is cry because it wasn't the best moment of your life. In fact, the cigar sucked and you wasted $400. You cry yourself to sleep thinking about how this is not a great moment.
Wandering the streets in a city new or familiar.
...no. At this point, you need focus on where you are wandering and why you can't remember if it's a new city or a familiar one. You have bigger issues at hand but then it strikes, "this $400 cigar sucks!" Now you start vandalizing things in this new/familiar city and you become a terrorist threat to the local authorities. Not a great moment.
Surrounded by close friends for several hours and enjoying what we all love.
I do enjoy this. But when they learn that what I am smoking is a $400 cigar and what I passed out to them was
only a $40 cigar, it becomes odd. There's a tension in the air and no one wants to talk about it. Things get awkward as the night progresses and you say something simple like, "Hey Mike, those shoes are pretty cool. Where did you get them?" to which Mike says, "Whatever bro, these only cost $90 and you probably wouldn't spend less than $300 for shoes like this because they aren't up to your 'standards'". Then all hell breaks loose and all you can think is, "this is not a great moment".