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To get this you have to get through 9 levels for Elle. 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 Elle are

Level 1 Adversary
350 Hearts
Level 6 Suave

Level 2 Nuisance
1,190 Hearts
Level 8 Funny
Work at Cleaning

Level 3 Frenemy
4,344 Hearts
Level 10 Tenderness
5 Rose

Level 4 Acquaintance
15,854 Hearts
Level 12 Suave
3 Chocolate

Level 5 Friendzoned
61,830 Hearts
Level 14 Wisdom
2 Drink
4 Moonlight Stroll

Level 6 Awkward Besties
241,136 Hearts
4 Beach
2 Flowers
Work at Casino

Level 7 Crush
940,430 Hearts
4 Sightseeing
Cake
Level 20 Angst

Level 8 Sweetheart
3,667,677 Hearts
4 Movie Theater
Plush Toy
Slot Junkie (Casino)

Level 9 Girlfriend
14,303,942 Hearts
Cute Puppy
Level 24 Mysterious
Dice Master (Casino)