Need user to select from a list of 50 options.

I have an odd situation where I need the user to be able to select for a list of 50 options. I can't use intents. I don't think VF has the ability to integrate a dropdown menu in a chat, although please correct me if I'm wrong. I'm wondering if I can use an API call to trigger a server side script to open a pop-up window that has the dropdown menu and pass the selection back to VF. It seems like a clunky solution, if anyone has a suggestion I apprecite it.