I cried in 5 out of 6 episodes of Takopi’s Original Sin. The me of 2020 wouldn’t believe it.
First time it happened was on completing Violet Evergarden the Movie on late 2021. Haven’t cried for more than 10 years prior to that, and it was the first I did so because I’m very happy for Violet.
What’s yours?
Can’t say for sure as my memory is not the best, but the first anime I remember me crying was the No Game No Life movie. The most recent (even if this is already a while ago) was Planetarian - Storyteller of the Stars.
And the first anime-related content which made me cry was the finale of the visual novel Corona Blossom (which was also my fist VN and has a special place in my heart).