Several Controls assigned to each selcted item of a listbox

Hello to everyone!
I'm pretty new using vba. I must say that everything I've done in my project, is due to reading many nights this forum and your answers to problems.
I have a listbox that contains the files (documents) of a folder (plus its' subfolders). The listbox takes the values from a table in a worksheet. On the userform there are many options (controls). I wonder how to assing the options to each selected item in the listbox. To tell a long story short, I want to achieve somethng like an email page. Selecting a value of the listbox, linking to the controls. And then selecting an other value from the listbox, linking again to the same controls. Of course, I have many problems yet to deal with, as you can see in the attached files.
Sorry if I got you tired! Hope you'll still help me!!