To get this you have to get through 9 levels for Iro. 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 Iro are
Level 1 Adversary
450 Hearts
25,000
Level 2 Nuisance
1,800 Hearts
Level 10 Motivation
Beach Patrol (Life Guard)
Level 3 Frenemy
7,650 Hearts
Level 12 Buff
5 Hand Lotion
Level 4 Acquaintance
32,513 Hearts
Level 14 Badass
5 Fruit Basket
Level 5 Friendzoned
146,306 Hearts
6 Moonlight Stroll
3 Drink
Level 16 Suave
Level 6 Awkward Besties
658,378 Hearts
6 Beach
2 Shoes
Work at Sports
Level 7 Crush
2,962,702 Hearts
6 Sightseeing
Cute Puppy
Level 24 Motivation
Level 8 Sweetheart
13,332,157 Hearts
Necklace
6 Movie Theater
Baseball Hitter (Sports)
Level 9 Girlfriend
59,994,707 Hearts
New Car
Level 26 Badass
Face Puncher (Sports)