He is saving far too often. Clearly does not have experience with games glitching with flags not triggering/doors remaining locked & requiring loading a relatively ancient Save. This isn't a game that can glitch (maybe?), but its still possible to save after flags that lead to bad ends. Saving before the date means he saved after he met that girl without telling kusorea and after making moves to contact her and ask her to meet. Saving before entering a diner means saving after telling her to eat at a place he picked and letting her know what place it is, and after getting the two people dangerously close to each-other that aborting might prove difficult.
If he has any sense, he should gather what intel he can, load, and then sort of as a response to the bodyguards tell them to hold it, and that he actually brought her there to let her identify someone who seems to carry a grudge and want to assassinate her with them trapped in a restaurant. So their services might be needed depending on kusoreas decision.