Can someone please explain this:
An so einEM grauEN regnerischEN Tag...
So, Why first Dative and then akkusative, or am I totally out any of this? Why not: An so einEN grauEN regnerischEN Tag...
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This has nothing to do with dative or accusative - What you consider an accusative ending just looks like one but actually isn't. "An" in your example requires the dative.
In a nutshell, the strong declension (and thus the dative ending) is being "absorbed" by the article, and all that's left for the poor adjective is weak or mixed declension.
Die Kerze leuchtet mit schwachem, flackerndem Licht
("mit" requires the dative, no article, "schwach" gets the strong dative declension ending)
Die Kerze leuchtet mit einem schwachen, flackernden Licht
("mit" still requires the dative, article "eats away" the strong declension ending of the adjective, which is now declined "mixed", thus gets an ending that incidentally looks identical to accusative, but still is in dative.)
Your example is very similar, "an" in your example requires the dative (because it does not denote a direction as correctly pointed out in a comment), but the strong declension of the two adjectives is "absorbed" by the article. if you look up mixed declension endings for masculine singular in inflection tables, you'll find that accusative, dative and genitive are identical with "-en".
If you want to look up strong, mixed and weak declension endings, check the inflection tables of your chosen grammar, or have a look here.
In addition, there are numerous rules when to apply which declension table one but it fortunately boils down to one case marker in the row is sufficient.