This guide explains how to get Succubus Crying achievement step-by-step.
Getting Succubus Crying Achievement
Lovelia can stay with you.Stop by the bookstore.Grab the manga within reach / Grab the manga farther away (i don't think this one matters, it just gives you different cgs / achievements).Volunteer to train her.Fold the laundry.Can you go in alone?If only you were human.
The rest of the achievements can be gained by picking either all top choices, or picking all bottom choices.
Source: https://gameplay.tips/guides/6656-troubledays.html