This trophy is awarded after the event with Gio involving the Raptorstein assignment.
Date - Friendship Level - Location - Description
Year 1, Month 7 - 0 - R &T Sundries - A short event occurs where you meet Gio.
2 Weeks later - 0 - Workshop - Gio repays you and you can do his Friend Quests. (He is located in the main street past Rorona's home.)
Year 2, Month 10 - 0 - Gio helps you obtain Raptorstein and can be recruited from now on. Costs several Days! I will update the exact number when I go through new game+.
The trophy unlocks after returning to town.