Thanks to naguide.com for this.
MAJORDOMO, in Hotel, select the cosplay dialogue options so the receptionist likes you. Having set up that flag, in Bunker 1 when you see her again, choose these dialog options:
-“can’t you just let me pass?”
-“I can’t show you my ID but…”
-“It’s a challenge, alright”
After that, keep spamming the interruption dialogue option until you win with the “You’ve just activated my trap card” line and you get the achievement.
Also make sure to go for the card game option and not the spinning top option when talking to her in the hotel.