*You don't have to buy everything, do you? I didn't before the first date. However, I had boughten all the items before the second date, so you could be right.
i just bought all of the items straight off, before i did anything else. i used my gift money (for having a un2 save) and money i got from cashing in scrolls that i got from going to the nindo (talk to iruka and select the second opion and then scroll collecting and then just go on top of ichiraku and they are there)(that is also how i bought everything from the general store). what do you have to do before you can go on the first date with him?
Well, first of all have you done the first date with him? That's where you meet him at the top of the wall entrance to Konohagakure (Hidden Leaf). Give him the present and then meet him along the river in the Village Center.
For the second date, meet him in the same spot and give him a present. Then go to the Training Field. If he isn't there but Guy is, do Guy's mission and he will show up after it. Just date him for the final time and it's yours.