ON THE DIFFERENCES BETWEEN HOLY SOULS AND DEMONS; BEWARE 20 QUESTIONS
I have neglected this crucial topic, especially as someone who posts most Novembers on the holy souls, but it has taken me a few years of study to understand Blai's points of expertise, which he lays out very clearly in this video from the 14 minute mark.
Blai is one of the most knowledgeable and well-versed on how a demon might manifest in the guise of a holy soul to a living person with the aim of manipulating them and gaining a foothold in their life. There is a clear distinction between both sets: demons are damned spirits and to borrow Blai's terms, they are "irredeemably evil" and"con artists", and have only malevolence as their motive: they are literally a foul intruder from hell attempting admittance by posing as a holy soul. Once inside someone's body, they misuse the person in vile ways. They are comparable to someone who shows up at the door of someone having a party, and they affect benignity and familiarity until they get inside and wreck the celebration.
Conversely, the holy soul has had their last judgment, they have stood before the Lord and know that which they need to rectify in Purgatory and that they can be aided by the prayers of others. They are on their way to Heaven but are undergoing purgation to make them pure enough to be in God's company for all eternity. They usually make known they want prayer and perhaps Holy Mass to be offered for them. As in the annals of the saints, they appear only ever with pious intentions, and the saints may know enough to be aware of a fallen angel taking on the appearance of a dead person so as to win their trust and then wreak havoc.
As Blai explains, the demon may pretend to be a dead loved one, like a grandmother, and they may know certain private information, because as invisible spirits, they were present at a time when they learned something that could be used as a way to gain trust at a later time.
The part that I found most instructive is that demons try to play 20 questions with the person they are hoping to fool. They desperately want to make the living person absorbed in their conversations with the aim of getting the person to make agreements and then little by little the person concedes control of their bodily facilities. Holy souls do not play this nasty game; they cannot sin. They also only say that which is necessary. True, they can reveal many things about Purgatory, such as sins committed in this life and the corresponding purification needed after death.
From my limited experience, I'd add a few things. I'm always wary of people who play 20 questions and who like tearing down other people's privacy maybe by posing the same question over and over, not taking no, and only stopping when they get yes. In my much younger and more arrogant years I definitely knew at least one conwoman who used this tactic; she'd ask the same question as though it had never been answered and even affected a hang-dog look, like she didn't remember the answer, but she stopped the pressuring inquest when she got the answer she wanted to control me. Even in a living human, this ploy is symptomatic of the satanic, because if an honest answer has been given, the act of asking the question repeatedly is dishonest because the person is acting as though they do no know the answer; when it is just not to their liking.
Also, fallen angels have angelic intelligence, and know who to play. I'd add here that the demon is more interested in someone who isn't humble enough to accept that demons are cleverer than them and can trick us so easily. There are humble people who may engage demons, but do so unaware of the superior intelligence of an evil spirit.
While I totally agree with Blai that demons are con artists, I'd hasten to add that for the living con artist there is still hope. I had Holy Masses offered for my con woman. But for the demon, they are in Hell for all eternity. They just want to drag us there, too. Even by pretending to be a saved soul in Purgatory.
For better and more informative work on this topic, check out The Catholic Guide to Miracles, a book by Adam Blai, pictured below. It is a marvelous work. Every chapter is like a golden chain that links us to knowledge of the Faith gathered over the centuries. You may get your copy here.
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