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Why does Montresor seem concerned about Fortunato's health?
Quick answer:
Montresor appears to be concerned about Fortunato’s health because they are supposed to be “friends.” Friends care about each other, and so, in order to avoid making Fortunato’s suspicious of his motives, Montresor must continue to act like a friend.
Montresor appears to be concerned about Fortunato’s health because he wants to maintain a ruse of friendship, and even admiration, so that Fortunato does not become suspicious. Montresor has carefully plotted a meticulous revenge on Fortunato to ensure that Fortunato knows who has brought about his demise and to ensure that Montresor will face no negative consequences for his revenge. Anything less, he feels, is not real revenge. Montresor says,
It must be understood that neither by word nor deed had I given Fortunato cause to doubt my good will. I continued, as was my wont, to smile in his face, and he did not perceive that my smile now was at the thought of his immolation.
If Montresor begins to treat Fortunato as an enemy, then Fortunato might be on his guard and become more difficult to deceive. So, Montresor continues to treat Fortunato as a friend, and friends...
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care about the health of their friends.
In addition, by continuing to recommend that Fortunato protect his health and return to the ground level, Montresor also creates the opportunity to have Fortunato later realize that his own pride played a major role in his ruin. Having chained the confused Fortunato to the wall inside the niche, he says, “Pass your hand […] over the wall; you cannot help feeling the nitre. Indeed it is very damp. Once more let me implore you to return. No? Then I must positively leave you.” In saying this, Montresor makes it clear that if Fortunato had not been so eager to prove Montresor wrong about the amontillado, so eager in fact that he jeopardizes his own health in order to have the chance to gloat, he would still be above ground and safe.
Therefore, not only does Montresor seem to care about Fortunato’s health in order to avoid raising his victim’s suspicions, but he also does it in order to impress upon Fortunato his own faults and torment him further.
Many elements of Poe's story serve a double purpose for reasons of economy. Poe's main reason for giving his character Fortunato a bad cold was to make it difficult for him to talk. Here is the most significant dialogue pertaining to Fortunato's cold:
"How long have you had that cough!"
"Ugh! ugh! ugh! -- ugh! ugh! ugh! --ugh! ugh! ugh! --ugh! ugh! ugh! -- ugh! ugh! ugh!
My poor friend found it impossible to reply for many minutes.
The bad cold of the intended victim makes his motivation to sample the Amontillado appear even stronger. It gives Montresor excuses to urge him to turn back (thereby showing his friendship and lack of any sinister motive). It causes Fortunato to drink more wine, thereby becoming drunker and easier to beguile. But most importantly it prevents Fortunato from asking a lot of awkward questions. Poe specified in his famous review of Hawthorne's Twice-Told Tales that not a single word should be included in a short story which did not contribute to the single effect; yet he uses fifteen "ughs!" This means the cold is very important.
If Fortunato hadn't been hampered by his cough he would almost certainly have asked such questions as:
When did you buy this Amontillado?
Whom did you buy it from?
Who was the exporter?
How much did you pay for it?
Who was the dealer?
Why did you store the cask so far from the bottom of the staircase?
Where are you taking me?!!
Poe avoids all such questions by the simple expedient of giving Fortunato a bad cold. Evidently Fortunato knows more about Amontillado than Montresor, so Montresor would have had a hard time answering questions about his non-existent cask of Amontillado, and Fortunato's suspicions would have been aroused.
Does Montresor pretend to care about Fortunato's health?
There is no doubt that the concern Montressor expresses for Fortunado's health is feigned. He wants to make sure that Fortunado has no hesitation in following him deeper and deeper into the cellar. Hie is actually unconcerned about the man's health, for he plans to kill him, but if he lets on that he is uncaring then there is a good chance that Fortunado will just turn around and go back up thereby foiling his carefully planned revenge,
At another level, the feigned concern about Fortunado's health is not all that much different than the feigned friendships that are mocked in this piece - the concept that, in certain levels of society, people will treat you one way to your face and another way behind your back. Poe was no stranger to this as the son of an actress. Although he lost his mother when he was only two, he carried with him the stigma of being the son of an actress - beloved on the stage but, in the eyes of society, not much better than a common prostitute. Many of the people in Poe's life were hypocrites, and this gave him plenty of fodder for writing characters who pretended to be or feel one thing when, in reality, their interior motives were much different and generally far more self-serving.
If you mean was he pretending or was he truly concerned, my opinion is that he was clearly pretending.
I think that someone who is planning to wall another person up in his wine cellar and let him starve to death is not too likely to really be worried about that other person coughing. So why show all the concern?
I think that Montresor is using reverse psychology. He does not want Fortunato to back out of going to see his new amontillado. So he keeps urging him to go home and he keeps saying he'll get the other guy to look at the wine. Both of these are in my opinion just ploys to make sure that Fortunato will really be motivated to go look at the wine.
What is ironic about Montresor's concern for Fortunato's health?
Irony is a state of affairs, a comment, or an event that is contrary to what you expect. We know from the beginning of the story that Montresor hates Fortunato ("The thousand injuries of Fortunato I had borne as I best could, but when he ventured upon insult I vowed revenge"). He will get his vengeance so that Fortunato knows what is happening but in such a way that Montresor himself will never be caught. In order to do both of these, he must be planning murder.
We don't know what he has in mind, precisely, when he takes Fortunato to his family dungeons in search of the cask of amontillado, but we can be certain that Fortunato will be dead by the end of it (or left to die). Thus, each time Montresor voices concern for his health (Fortunato has a wicked cough, and they are going into the cold crypts of Montresor's family home) we are struck with the incongruity of what we expect (Montresor being keen to get Fortunato to the place he plans to kill him) and what we encounter (Montresor being concerned that Fortunato will get sicker and all but ordering him to turn around and go back).