This achievement will pop as soon as the "Juice Drinking" mini game pops up. I had a real hard time getting this mini game to pop and spent hours on it. I tried several girls but the girl that worked for me was the 5th girl. This mini game only pops when you pick the top left dating scene which looks like a street with some shops. Also, to note that in this playthrough I did not skip dates at all and kept on going year round picking this dating scene until this finally popped. It's very random as mine popped in October so it can pop at any month.
I suggest not to waste time and start with the 5th girl, do not skip any dates and keep on picking that dating scene until this annoying mini game does show up.