Ask the Experts / Make a guest buy a hat...

[EDIT] I couldnt figure out how to delete this but I managed to get some hats on them. I just had to build them a whole little amusement park at the entrance. Annoying, but I have my cowboy now. All I have to do is leave him there walking alone until I'm finished with the whole project and he will be sad.

Alright, so for this project I really want a sad cowboy walking alone in this town but I can't figure out how to make the guests get a hat. I pick out all the guests with the right pants/shirt color combos and put them in this area and use Dragons/4cars to make them happy and vitalized and everything, give them money, even make the hats free. I plopped a rollercoaster in hoping they would ride it and be happy and want a hat but none of them have any interest. Does anyone have any insight on making a sad cowboy?