This is a missable achievement during the main storyline of chapter 15.
Guide from psnprofiles.com
After you fight against Kashiwagi on top of the Kazama family building a yakuza member will tell you Nishki usually hangs out at Serena. So incase if you mess up by either hitting the QTE by pure instinct or if you knocked Nishki out too fast or if the achievement is bugged/ doesn't unlock just make an emergency save before you go in. When you get to Serena there will be a scene where Majima will ask Nishki where Makoto is and things go south. Halfway through the fight Nishiki will eventually throw you towards the bar, causing a QTE to trigger where Reina swings a bottle at Majima's head. You must fail the QTE, so just let the time run out or press the wrong button prompt and she'll hit you, causing this achievement to pop.
(Note: There are 2 QTE's that will play during the one where Reina will smack you with the bottle and one that can appear where she'll attempt to throw Nishki a bottle of stamina Royale in which you can intercept and gain some of your health back.)