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Partly to help keep it straight in my own head. Crowley really does like to screw with people, you know that?
* Pre-series (AV, SPN and GO) - Before they met in any shape. Castiel's heard of the Serpent of Eden, and presumes said Serpent was either a) a straight-up Fallen angel who took 'serpent' as a metaphorical title (at least plausible, according to most angels), b) a Fallen angel who possessed a serpent at the time for Temptation purposes (least likely in most opinions, but more or less the actual case), or c) an actual serpent who just felt randomly evil that day (mostly likely in most opinions at the time, because most of the Fallen are still landscaping Hell at this point)
* Prelude (pre AV, post GO, set during Dean's time in Hell pre-S4 SPN) - angel-form Cas meets snake-shaped demon in Hell (Crowley being that shape mostly to keep Alastair from getting inventive), and presumes that said demon is either a) a particularly warped human-type demon, b) one of the more esoteric evil spirits, or c) a Fallen with a fetish. Since he doesn't get Crowley's name in this encounter, he doesn't connect him with either the Serpent of Eden OR the human-shaped Crowley he meets in 5x10 (SPN)
* SPN 5x10 - human-shaped Castiel meets (well, stalks) human-shaped Crowley, who is very deliberately pretending to be a human-type demon for the express purpose of getting Sam'n'Dean to do what he wants. Enochian warding and time constraints mean the angel doesn't get too close a look at him, and vice-versa, and both of them are quite happy with this state of affairs. Crowley hasn't yet connected human-Cas with angel-in-Hell-Cas, and Cas hasn't connected human-Crowley with either the Serpent, the Fallen, or snake-demon-in-Hell
* Arrangements Part I (post SPN 5x10 definitely, possibly post 5x13 also) - human-Cas meets fallen-Crowley, along with Aziraphale. Realises that the human-type demon ruse from 5x10 was a ruse, and Crowley is both a Fallen and the Serpent of Eden. Is told that (b) of the original Serpent theories is correct. Still makes no connection with the snake-demon-in-Hell, which Crowley is only too happy about. Crowley, OTOH, recognises the name Castiel as the angel-in-Hell, and is basically playing with Cas from here on out.
* Arrangements Part XII (post SPN 5x16) - Castiel sees fallen-Crowley in snake-form for the first time. Connects him with snake-demon-in-Hell (for bonus blackmail points), realising that Crowley has, therefore, pretended to be a human-type demon, a snake-type demon AND a fallen angel in his presence, sometimes more than one at once. Comes to the conclusion that Crowley is a fallen angel in a snake body warped to human-shape, making him a angel-human-snake hybrid, and both (a) AND (b) of the original Serpent theories correct.
Also concludes that Crowley is a squirmy bastard who's allergic to letting people know more than two facts about him at once, far too gleeful about letting people think he's someone he isn't, and playing the multiple-shape-game purely to screw with angelic minds (all of which are ALSO more or less true), and therefore richly deserves whatever blackmail is about to fall on him
Castiel-Crowley timeline from Arrangements-verse
OR How Crowley repeatedly screwed with an angel's perception of the universe in general, and of one demon in particular* Pre-series (AV, SPN and GO) - Before they met in any shape. Castiel's heard of the Serpent of Eden, and presumes said Serpent was either a) a straight-up Fallen angel who took 'serpent' as a metaphorical title (at least plausible, according to most angels), b) a Fallen angel who possessed a serpent at the time for Temptation purposes (least likely in most opinions, but more or less the actual case), or c) an actual serpent who just felt randomly evil that day (mostly likely in most opinions at the time, because most of the Fallen are still landscaping Hell at this point)
* Prelude (pre AV, post GO, set during Dean's time in Hell pre-S4 SPN) - angel-form Cas meets snake-shaped demon in Hell (Crowley being that shape mostly to keep Alastair from getting inventive), and presumes that said demon is either a) a particularly warped human-type demon, b) one of the more esoteric evil spirits, or c) a Fallen with a fetish. Since he doesn't get Crowley's name in this encounter, he doesn't connect him with either the Serpent of Eden OR the human-shaped Crowley he meets in 5x10 (SPN)
* SPN 5x10 - human-shaped Castiel meets (well, stalks) human-shaped Crowley, who is very deliberately pretending to be a human-type demon for the express purpose of getting Sam'n'Dean to do what he wants. Enochian warding and time constraints mean the angel doesn't get too close a look at him, and vice-versa, and both of them are quite happy with this state of affairs. Crowley hasn't yet connected human-Cas with angel-in-Hell-Cas, and Cas hasn't connected human-Crowley with either the Serpent, the Fallen, or snake-demon-in-Hell
* Arrangements Part I (post SPN 5x10 definitely, possibly post 5x13 also) - human-Cas meets fallen-Crowley, along with Aziraphale. Realises that the human-type demon ruse from 5x10 was a ruse, and Crowley is both a Fallen and the Serpent of Eden. Is told that (b) of the original Serpent theories is correct. Still makes no connection with the snake-demon-in-Hell, which Crowley is only too happy about. Crowley, OTOH, recognises the name Castiel as the angel-in-Hell, and is basically playing with Cas from here on out.
* Arrangements Part XII (post SPN 5x16) - Castiel sees fallen-Crowley in snake-form for the first time. Connects him with snake-demon-in-Hell (for bonus blackmail points), realising that Crowley has, therefore, pretended to be a human-type demon, a snake-type demon AND a fallen angel in his presence, sometimes more than one at once. Comes to the conclusion that Crowley is a fallen angel in a snake body warped to human-shape, making him a angel-human-snake hybrid, and both (a) AND (b) of the original Serpent theories correct.
Also concludes that Crowley is a squirmy bastard who's allergic to letting people know more than two facts about him at once, far too gleeful about letting people think he's someone he isn't, and playing the multiple-shape-game purely to screw with angelic minds (all of which are ALSO more or less true), and therefore richly deserves whatever blackmail is about to fall on him
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