Nice design, but that's the kind of functionality that's best integrated within a chat or videoconferencing application, since within a conference you can be pretty sure that you send the file to the right person.
For a demo, go to <https://galene.org:8443/group/public/hn/>. Login twice in two different browser tabs (leave the password field empty). Click on the username of your partner, and choose Send file.
For a demo, go to <https://galene.org:8443/group/public/hn/>. Login twice in two different browser tabs (leave the password field empty). Click on the username of your partner, and choose Send file.