Actually. The correct answer is no.
Since Myu was left at home in the middle of the season.
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In my opinion, there are only two options:
- you can watch it before S2
- you can watch it after S2
The reason is that the action of this special episode takes place when they are going through a green area and they have not entered the desert yet (what happens at the very beginning of S2). The argument to watch this after S2, with mind that this is a story from the past, is that the episode shows the sight of Myuu's mom and Shirasaki is openly saying she feels weak, which is part of story inside S2. In other words, it contains a spoiler of just 1% of what would normally happen next. But if you watch it after S2 then it won't be chronological (the characters and their appearance are different, like they will be in storyline just after S1).
So that's the choice you can make. Both options are fine, but probably I would recommend to watch it before S2.
###|||私はアニメと日本文化が大好きです|||###"Kago-ni noru hito, katsugu hito, sono mata waraji-o tsukuru."###
Watch after S1, then the S1 Specials, and then S2.
BankaiGoku said: In my opinion, there are only two options:
- you can watch it before S2
- you can watch it after S2
....
So that's the choice you can make. Both options are fine, but probably I would recommend to watch it before S2.
I watched the Season 1 specials, then watched/skimmed the last 2/4 episodes of S1 to refresh my memory.
I then watched the S2 special, as per this recommendation.
I have not started Season 2.
BankaiGoku's spoiler explanation of why you would watch this after S2 is too much detail, highlighting irrelevant information.
S1 ended with them all driving in the truck, and this starts with them driving in the truck, then doing standard side-story stuff.
At the end of this, you can assume they get back into the truck and continue on to whatever happens in S2 but there is absolutely no reason to delay watching this after S1, unless you're the type to notice AND question small bits of information that occur in like 3 seconds, that are disconnected from the overarching plot, and are then discarded.
The group are driving in the truck, when they pull over and Yue gives them lessons on using magic.
In town, they try on each others clothes.
While driving, Myuu sleeps like a baby on Yue's lap whilst Yue is overwhelmed by the cuteness
Yue wants to know why Myuu refuses to call her Mom, when she could have 2 moms instead of the one.
Yue knows what Myuu's mom looks like (presumably she appears and they meet in S2)
In S1, she's only mentioned to be alive before Myuu was kidnapped.
BankaiGoku mentions that during the clothing exchange section, Kaori is called weak and that this is specified in S2.
This could've been in reference to when they first met and Kaori's group loss badly to monsters that they then wiped out easily, and also that Kaori is only a healer type.
edit: I watched Season 2 now. There is no way you should wait to watch this afterwards.
If you paid attention to continuity and even wanted to watch this during S2, you would have to add a new adventure in the middle, to fit this, whereas if you just assume it happens directly after S1, nothing will be out of place within any kind of reason.
Because of some changes by then end of S2, you would have to "remember back then" or, again, add some events in order to make it make sense to happen afterwards.