When the date event occurs, the character who has the highest affinity with Cloud goes on the date with him.
There are no general guides here - you have to do everything very specifically!
In Midgar: If you are unsure, repeat step 19 as many times as you want, and fail at the fifth question.
General Guidelines When you have to create a party, always take Aeris and always leave Tifa aside (except when you don't have a choice, at the early stages of the game).
This alone should make it so that Aeris is chosen, but it doesn't hurt to overdo it, so read on.
This means that you will have to be a jerk toward both of them.
And of course, you can only date Yuffie if you got her to join you in the first place.
Each of these characters, throughout the course of disc 1, has an hidden parameter that we will call "affinity" with Cloud.
This parameter changes during the game for each character, and can go up and down depending on two factors: your responses when given multiple choices questions, and the composition of your party at certain stages of the game.
When you get tired of it, finally take her with you.
Herein lies the big challenge: are you strong enough to lure Barret into your net?
General Guidelines When you have to select party members, always take Tifa and always leave Aeris aside whenever you have a choice.