FYI I think I had a bug.. I bought the cane but it wasn't in my inventory. I couldn't rebuy or progress with the girl (i forget the name, rachel maybe) because of this.
Yeah I got the name wrong.. I am still a little confused, I seemed to get stuck in a state where I couldn't progress anyone. The second football skins vs shirts scene didn't trigger and I am not sure why. In the end I loaded an old save where I had already unlocked more. It might be as simple as upgrading the pool before the cafeteria. The hints get a little sketchy.