How to select uploaded files and then send them to email

I know it’s possible to upload multiple files with Gravity Forms. I would like to know if there is any way (add-on or plugin) to select which uploaded files we want to send to email, and choose who we send the files to in the front-end. I know we can do a notificitation with all uploaded files, but that’s not exactly what we are looking for.

Any clues?
Thanks in advance.