No no! Its not about how well dressed you are. Just if say you are a lady and you're trying to woo Jay, you keep your avatar female. But if you are a lady and trying to woo mika then you have to change your avatar to a male appearance for the duration. Of the fifteen posts. And vice versa.
Haha. Just think of it like a date! Just roleplay what you would do for a date if you were trying to impress the person you had a crush on. xD I figured it could be entertaining and provides a bit of roleplay~