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I've never played a dating sim, but I have played a lot of NES games and watch my friends unknowingly and completely blow relationships.

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Yep, this is basically what dating sims are like. And dating.

This was extremely professional, I loved it!

for a minute I actually thought I unlocked a medal

I was having fun, and then it got dire. Then I got existential. Thanks, now I have to contemplate the motivations and implications behind all my relationships now....

Or maybe just watch more animations.

The most confusing yet brilliant narrative ever contained in a two minute animation. I was so glad for subtitles, because even then it was incomprehensible, but in a good way.