To get this you have to get through 9 levels for Quill. Each level has up to 4 goals you must complete to reach the next level. The possible goals are, reaching a specific number of hearts, reaching a specific amount of money, giving specific gifts, taking the girls on dates, reaching a specific level in your hobbies/jobs.
The goals for Quill are
Level 1 Adversary
300 Hearts
Level 5 Tenderness
Level 2 Nuisance
930 Hearts
1000 Dollars
Level 6 Funny
Level 3 Frenemy
3,116 Hearts
Level 8 Wisdom
Shell
Work at Cleaning
Level 4 Acquaintance
10,437
Fruit Basket
Chief Sweeper (Cleaning)
Level 10 Buff
Level 5 Friendzoned
37,573 Hearts
Earrings
Level 12 Tenderness
3 Moonlight Stroll
Level 6 Awkward Besties
135,263 Hearts
Flowers
3 Beach
Work at Zoo
Level 7 Crush
486,945 Hearts
Plush Toy
Level 16 Angst
3 Sightseeing
Level 8 Sweetheart
1,753,003 Hearts
Tea Set
3 Movie Theater
Level 18 Funny
Level 9 Girlfriend
6,310,809 Hearts
Necklace
Red Panda Helper (Zoo)
Level 20 Tenderness