This trophy is awarded after the first scenes with Pamela.
Date - Friendship Level - Location - Description
Year 2 until end of game - 0 - Catacombs->Ghost Assembly (lower right fork on overview map) - You will find a teddy and bring it back with you
The next day - 0 - Workshop - A series of scenes starts with Pamela and Homhom
The trophie unlocks after the scenes have ended.
Notes:
- Multiple character dates are close together during this time so you may want to refer to a walkthrough if you are going for the true ending on the first play through.
- Most people prefer to get Tantris first.
- When you go to the Catacombs be sure to find the Pnakotic Manuscript.