There is actually something like that. While it's not like he died and got reincarnated several times, he just kept getting summoned into different worlds.
Truck-kun never takes a break, always making sure to Isekai the people. So next arc is going to be Sayuri + the lil' girl + her dog in a strange fantasy world?
That's the face of someone's who been utterly and completely mindbroken. Whose worldview has been shattered. Literal "does not compute" face.
In way it's kinda pitiful. She's so broken already that seeing someone doing things for the sake of it broken her twice again.