Obtained: Chapter 9 – Approach Megumi on N Isezaki Road (day)
After the brief cutscene, speak with Megumi. When the cutscene concludes, leave the area then return to trigger the objective. Speak with Megumi again then head to the objective on Central St. and defeat the thugs. Afterwards, make sure you have 1,000,000 yen on you then take a taxi to the hospital (last option on list). When you regain control, head to the objective on Hyakkei St. near Akaushimaru (Isezaki Road).
Reward: Unlock Megumi as a Poundmate