Catherine

This achievement is unlocked on the 8th Day, but requires an action every day. On the days you are at the Stray Sheep, you will have the ability to choose from four drinks to have at your booth seat. To take a sip press while sitting at your booth with your friends. Once you finish one (three sips), you will get a piece of trivia on that drink, and will be able to order another from Erica. When she comes to your booth request sake by pressing and she will bring it to you. Boss the bartender can also take your drink orders up front when you sit there. Each day, make sure to drink(three sips) Sake at least once each night. On the 8th Day, you will unlock the achievement once you receive your last sound bite.

Note: Remember you can only get one bit of trivia per night for each drink. It is possible to get one tip from each drink each day, so you can unlock all four drinking-related achievements in one playthrough. However, you have to start getting a tip for every drink starting on the 2nd Day and onwards or else you could miss their respective tip achievement.