haha i get that, it can be pretty weird with fate but i don't know how much you know about fate so i'll explain the whole thing
i myself first watched fate in release order so i watched fate/zero --> unlimited blade works --> heaven's feel movie trilogy
but tbh i don't think this a good order for first-time viewers because they don't explain all the terms in fate zero and expect you to already understand what's happening, so i ended up having to google a bunch of things while watching to understand lmaoo
from the main timeline - unlimited blade works is known as the rin route, heaven's feel is the sakura route and fate stay night 2006 is the saber route. they are called routes because they all share similarities since the source material is from a game where you can choose which character route to play and so they made all 3 routes into anime. meanwhile fate/zero is a prequel story set 10 years before unlimited blade works
so for first-time viewers i'd recommend this order:
first unlimited blade works prologue --> unlimited blade works season 1 and 2 --> heaven's feel part 1, 2 and 3 --> fate/zero
and then in the end you can watch fate stay night 2006 if you want, but most people don't like that one since it doesn't have ufotable level animation lol so you can skip it if you want
that's the important part of fate that you need to watch, aside from that there's a lot of spin-offs but a lot of it doesn't matter. but if you wanna watch the latest one which is fate/strange fake (the LN is in my favorites and the anime looks amazing) then you'll have to watch a few more things to understand
and that's all the homework (LMAO) you'd have to do to completely understand fate strange fake (otherwise you wouldn't be familiar with the characters and so their appearances wouldn't mean anything to you)
there's also like 3 movies connected to fate grand order, but i excluded them because they only help you be familiar with the fate grand order universe but doesn't contribute anything towards fate/strange fake, so if you really care then you can also watch them but remember it's not important and totally skippable
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i myself first watched fate in release order so i watched fate/zero --> unlimited blade works --> heaven's feel movie trilogy
but tbh i don't think this a good order for first-time viewers because they don't explain all the terms in fate zero and expect you to already understand what's happening, so i ended up having to google a bunch of things while watching to understand lmaoo
from the main timeline - unlimited blade works is known as the rin route, heaven's feel is the sakura route and fate stay night 2006 is the saber route. they are called routes because they all share similarities since the source material is from a game where you can choose which character route to play and so they made all 3 routes into anime. meanwhile fate/zero is a prequel story set 10 years before unlimited blade works
so for first-time viewers i'd recommend this order:
first unlimited blade works prologue --> unlimited blade works season 1 and 2 --> heaven's feel part 1, 2 and 3 --> fate/zero
and then in the end you can watch fate stay night 2006 if you want, but most people don't like that one since it doesn't have ufotable level animation lol so you can skip it if you want
that's the important part of fate that you need to watch, aside from that there's a lot of spin-offs but a lot of it doesn't matter. but if you wanna watch the latest one which is fate/strange fake (the LN is in my favorites and the anime looks amazing) then you'll have to watch a few more things to understand
so after fate/zero --> fate grand order --> lord el-melloi case files --> fate/strange fake whispers of dawn --> fate/strange fake
and that's all the homework (LMAO) you'd have to do to completely understand fate strange fake (otherwise you wouldn't be familiar with the characters and so their appearances wouldn't mean anything to you)
there's also like 3 movies connected to fate grand order, but i excluded them because they only help you be familiar with the fate grand order universe but doesn't contribute anything towards fate/strange fake, so if you really care then you can also watch them but remember it's not important and totally skippable