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Once you have unlocked one of the characters, you can begin dating them.
It usually involves a few back and forth text messages before an option opens to either offer or respond to a date request.
Once you have met a girl and organized a date, look for the purple heart icon on the map to progress.
To unlock Sana Mihama as a potential girlfriend you must complete Amidst A Dream Side Case where you buy her CD, listen to her music, and save her from an overly aggressive executive.