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It would be nice if the devs released a guide on how to unlock all the achievements, sometimes we have to wait months for someone to get interested and go through the game files to find out how to unlock them.
What Valgoat and Tanuvein are saying is what I done also, so I think its related to those objectives.
I'm not sure it has a time limit for it to happen.
I was just looking through my inventory and was wondering what the chocolates were for.
And of all the people I decided to just give them to Madison, pure luck how I got the achievement as I didn't intend to get it.
Keep on her good side during the initial conversations. Give her the chocolates in your inventory, she will be pleased. After this, the chocolates should appear opened on the locker on the right side of her bed.
Look at them closely to get the achievement.
In hindsight I can see why eek didn't really publicise this too much. At the end of the day, it's pretty weak, but oh well.
I was given the box when loaded into a game. You need to have the 1st conversation with Madison (introduce yourself). She will tell you to give her some time and then you can give her the box of chocolate. Achievement poped like 10 seconds later.