What do I do in the Plaza

Hint 1 of 5:

If you don't have all 8 items and Trent/Tiffany, nothing.

Hint 2 of 5:

Otherwise, give Trent/Tiffany each of the objects in the order...

Hint 3 of 5:

...he/she asks for them.

Hint 4 of 5:

If you waste any time, say good bye.

Hint 5 of 5:

If you give him/her all 8 items, you win.