Akuyaku Reijou Tensei Oji-san - Vol. 1 Ch. 7

[hoho1]

Truly a tsundere moment

 

[Siquall]

Tsundere is the easy mode.

 

[Lelouchezero]

My question is, when exactly did he learn about the terms and tropes that are used in these kinds of otome games?
Like, I get that he watched his daughter play, but how did he learn about flags and "SOON DAY RAY"?

he's first generation otaku. They actually mention that earlier when he was talking to his daughter about old manga with the "villainess" trope. Drills have ALWAYS been a villainess trope ALWAYS.