Clarification on Recycle Bin Emptying

I am running a Windows 8 OS for purposes of this inquiry. I don't religiously empty my recycle bin. I can go stretches of time without cleaning it. Today, I checked the recycle bin after doing some housekeeping on my fixed drives. I saw that there were other files that are showing deleted on a removable drive that could use the free space. I also saw some other files which I wasn't sure I wanted to remove permanently yet. So I highlighted some of the larger files in the recycle bin that are from my removable drive, and began the removal process. These files have been deleted for a long time already, compared to the files I had just deleted in my housekeeping. As I monitored the progress, I noticed that there were headers flashing as the removal was going on. Instead of seeing the file names of the files I was removing from the recycle bin, I was seeing 8-character stretches (which I call 'headers' for lack of knowing better), some of which seem to show parts of file names from a different directory. That alarmed me and I cut off the process, but it had gone through halfway and had cleaned out a few GB before I stopped it.

I have many data files on that removable drive, so much that I cannot remember most of them, but I certainly want to keep them. I have proceeded to access the removable drive again, and so far I do not notice anything wrong yet.

I took out my removable drive from my desktop for my travels earlier and plugged it back into my desktop today, but along with other removable drives. In the process, the drive letter assignment changed from before.

Was that a screw up of the recycle bin process and caused me to lose some files? Or is there nothing for me to worry about? Should I expect to see the proper file names in the recycle bin flash through as the removal process is being done?