Start by heading to the bottom right (southeast) section of Wall Market. Talk to the fat guy in red standing in front of the Honeybee Inn. Ask him about Tifa to find out where she is.
Make your way to the very top of these two screens to Don Corneo’s mansion. The guard standing out front of the entrance will inform you that men are not allowed into the mansion. Cloud and Aeris will then decide to dress Cloud up like a girl in order to get the both of them into the mansion.
Start by making your way to the clothing store. It's located at the top left corner of the bottom screen, and can be seen in the picture to the below.
Talk to the cashier and Aeris will ask her about getting a dress made for Cloud. She will then tell you about her dead-beat Dad who’s drinking his troubles away at the local tavern. Head over to the bar and convince him to come back to the clothing store. The bar can be found just north of the clothing store, as seen in the pictures below:
The circled guy in the picture is the dressmaker. Talk to him and Aeris will get him to head back to the shop. The best dress is earned by choosing one that “feels soft” and “shimmers”. I have no idea why it matters. But you're not a real man unless you wear a really pretty dress… right?
Make your way back to the clothing store to try on your fancy new dress. Next up on the agenda for turning Cloud into a girl is a wig. Make your way up to the gym, which can be found on the bottom right portion of the upper section of Wall Market, as seen in the picture to the below.
Talk to the woman in the blue dress. She’ll start you off on a squat challenge. I suggest you practice once or twice until you have it down. Just don’t go too fast and you’ll have no problem. Your competitor will screw up a few times, even if at the start it looks like he is a flawless squatter. Successful completion earns you a Blonde Wig.
You have enough items to continue the game at this point, but there are a few more you can pick up to help you feel more like a woman (they also improve your chances of being picked by Don Corneo, which will save you some time in the end).
Go to the building in the northeast and talk to the guy lying down inside. After that make your way to the Inn.
Spend the night and after you awake you’ll be given a choice of items to buy. Buy the most expensive one. Then go back to the man who told you to buy it and he will reward you with a Tiara.
Next go to the restaurant in the center of the lower portion of Wall Market, as seen in the picture to the below.
Sit down and order something. Afterwards tell the waiter that the food was ‘alright’ and he’ll give you a coupon for the pharmacy. The pharmacy is just south of the restaurant. When the pharmacy salesman asks you what you want select the digestive. Take it back to the bar where the clothing storeowner was and head to the bathroom in the back. Offer the woman in there the digestive and she will reward you with Sexy Cologne.
Finally head to the south and talk to the orange guy in the white shirt. He will give you the “Member’s Card”. Go to the Honeybee Inn and use your member’s card to get inside. The two doors on the left will offer you either Lingerie or the Bikini Bottom (it doesn't matter which you choose). You now have all the items you can get.
Take this time to stock up on items and new weapons before you continue the game. When you're ready go back to the clothing store and change into your new outfit. You are now ready to make your way into the mansion.
Once you get inside and are free to wander around go up the stairs and into the open door on the left. Tifa is at the bottom of this set of stairs. Once the Don is ready head up the stairs and into the center doorway.
If the Don chooses Tifa or Aeris you will end up in a room fighting a bunch of pushovers. If Cloud is chosen, however, you’ll go straight to interrogating Don Corneo. A lengthy interrogation session ensues, with threats of testicle mutilation being the highlight. When the Don presents you with a question to which you are given three answers, it doesn’t matter which you choose. You’re going in the hole.
Side Quest: Gold Saucer Date
This information is for the Gold Saucer date side quest (click here for more information).
If Tifa is chosen as the Don's date:
If Aeris is chosen as the Don's date:
If Cloud is chosen as the Don's date: