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If you get the best items in Wall Market, you can get Cloud to be chosen. I end up doing it everytime just because its funny. Ill explain it in detail to get everything and the best style of everything if necessary.

Alright, you go through Wall Market normally, right.
Dress: When you go to choose the materials for the dress, the best one is the Silk Dress, attained with the choices "soft" and "shimmers."
Wig: Next is the wig, which you have to do the squat competition. Make sure you win it to get the Blonde Wig.
(Now you can either go on or get the rest of the items. Instead of changing now, we gotta get the rest of the items in order to get Cloud chosen.)
Cologne: Talk to the guy that needs to get into the bathroom in the Bar. Afterwards, talk to the girl in the bathroom and find out shes sick. You can now go to the Restaurant and eat any meal to get a Pharmacy Coupon. With this Pharmacy Coupon, go to the pharmacy and choose the Digestive. Bring the medicine back to the girl in the bathroom, and youll get the Sexy Cologne, the best one.
Tiara: Go to the Materia shop and talk to the guy who runs it. He says he wants something from the Inn but cant go in himself. So stay a night there after talking to him and youll awake in the middle of the night and go to the vending machine. MAKE SURE YOU HAVE 210 GIL FOR THE NIGHTS STAY AND THE ITEM. You want to chose the most expensive one naturally. After the nights stay, go back to the Materia shop and talk to the guy again. Hell give you the best Tiara, the Diamond Tiara.
Underwear: This ones funny. You talk to the guy hovering around on the first screen of Wall Market down near the entrance to the Honey Bee Inn and hell give you his Members Card. You can use that to get into the Honey Bee Inn. Just go in and explore the two rooms on the right first, just for fun. Then go to either room on the left and spend the night. The &%$# room is one with a semi-story relevance if you care enough and it also has the best underwear. Talk to the employee before leaving your room after your stay and you should get the Lingerie.
Makeup: You can also get makeup at the Honey Bee Inn. After getting your underwear, go into the room to the north. Talk to the last employee and ask for makeup. Simple.

Now you should have everything thats the best, so you will get chosen for the night. Always works for me. Have a fun time with the scenes inside with the Don.

He sure can! The only downside to getting Cloud chosen to go back with Corneo is you miss out on an item. >> Uhhh i forgot what the item was...

www.ff7citadel.com There is a link that will show you how. It's funny, actually.

You can get the item upon your return to Wall Market to go up during the Shinra Tower attack. Just waltz into Corneos and take whatever you missed.

I've played both version so I might be confused but I want to say that I got into Honeybees and got the underwear in the PC version too.

Its a very long and complicated process, but it's worth it. It's hilarious. smile I had to use an online guide from gamefaqs.com to know which items to get and stuff...