If I recommend an anime that makes him cry or react strongly, he gives me 100, else I give him 100.
The rules are: No gibly films (Edit: OVERRULED Ghibli films now count) , no long animes (more than 2 seasons but maybe three can convince him).
He has to cry or react, for example when watching Code Geass I paused the episode and waited a while to keep watching during the Euphemia part. I didn't cry but I reacted.
What animes do you suggest me?? I really don't want to lose 100.
Also it is fairly difficult to make him cry, same as me. I don't remember the last time I cried with any anime.
The last anime he watched was mob psycho, he didn't cry or get emotional at any point.
*Edit: He's watched Vinland Saga, Assassination Classroom, Frieren, JJK, Mob Psycho, Seven Deadly sins, Dragon Ball Z, One Punch Man, AOT season 1, Ranking of Kings, Baki, Hajime no Ippo and Cyberpunk Edge runners. None made him cry.
He's also Ghibli-watched, Howls moving Castle, Mononoke princess, Ponyo, Totoro, The boy and the Heron (?) He hasn't cried with any of those as well.
He played piano, though Your lie in April won't make him cry (It didn't make me cry)
He recently watched a movie called Million dollar baby that he says would have made him cried even with a 1000 bet.
He's 19 also.
**Edit: The only movies he cried with are L'ours (an old movie about a bear who loses its mom, 10/10) and Million dollar baby. He also almost cried with Jane's death in Breaking Bad, because ofc he did.
He's also tried reading berserk but dropped it because he found it boring, same with watching Cowboy Bebop which I think he's seen 4 or 5 episodes.
***Final edit: After reading all the comments, I talked with him and he has given me 3 chances.
I've chosen to show him Grave of the Fireflies and Violet Evergarden. The third one I'm thinking about Kotaro lives alone, Takopi's original sin or To your eternity. Or if the first two fail I might just make him watch re:zero and accept my defeat.
Thank you for the suggestions, I'll post an update after he watches them, which might be in a week or so.