Instructions
Drive to the South Island cabaret. It's in First Town by the Aqua Sky club.
Enter the cabaret. When asked if you want a table, respond "Yes." Choose a dancer to sit with you.
Give the dancer a present, such as the popularity bracelet or lucky bracelet. You can get presents from the Ebisuya Pawn Shop. Ebisuya is located south of Club Sega.
Select from the menu of food and drinks. The refreshments you choose affect the dancer's attitude. Generally speaking, the more expensive something is, the more her opinion of you will improve.
Press the Circle button if she asks what her best feature is. This causes the screen to zoom in on her. Use the analog stick to look over her body. When you find your favorite feature, let go of the analog stick.
Choose from the list of rumors when she asks what you've heard recently. You overhear rumors while wandering the city. You also get rumors when you order food from a restaurant several times. You'll gain hearts no matter what selection you make. You can even choose the same rumor twice.
Return to the cabaret after your conversation is over. Keep giving her presents and buying expensive foods. Once she has eight or more hearts, then she'll be ready for a date. She'll ask you to see her after her shift.
Pick her up at the specified time to start your date.