What are most shocking routes you’ve played?

There are so many heartbreaking scenes from games I've played too… but I can't mention the titles or it'll become a spoiler TT

Toma's route in AMNESIA completely broke me, and it's still the most shocking route I've ever played. He was my absolute favorite at first—just this super gentle, sweet childhood friend. To see him turn into an extreme yandere and literally lock the MC in a cage was insane.
Even though Seri's route in DYNAMIC CHORD feat. Liar-S was also a huge shock to me, AMNESIA was my first otome game, so Toma's route is the one that left the deepest, most unforgettable impression.

3 Routes in Taisho x Alice shocked me the most.
I self insert for better immersion, had to remind myself I'm not the MC during those routes for sanity's sake:

Gretel's Route - the 1st Forest part (was cheering for Gretel in Forest part 2)
Snow White's Route - the Hut (I didn't need those details lol)
Kaguya - yeah... if that's what is needed to be done to get his best ending... it be best to let go and move on... a shame you're forced to clear it to unlock other routes

Maybe not as shocking as some of the examples mentioned, but Shuu Iwamine's route in Hatoful Boyfriend wasn't what I expected, and it's not something that's easy to explain :D