He is supposed to die 12 times...how many times has he died so far?
There was the guy on the plane
the guy tied to the chair
the bullied kid
the magician
the ex-convict
the game streamer
the juvenile delinquent
So that's 7 that I remember
What if this ends up being like the game "Roy" in Rick and Morty, and he marries her, has a family and lives for years before he dies and sees death to move on to death number 9?
Or as someone said below, maybe he just keeps meeting up with her in his next life and eventually ends up with her after death finishes his punishment.