File Explorer not showing recent folders

Here is my process. I scan documents onto my pc and save them to a file on my network drive. Then, I need to email these pdfs to other employees. I used to open Outlook, create a new email then click on "attach file". I would then get a drop down menu of the recent files I've worked with. There were some files on this recent list that I wanted to remove. I couldn't figure out how to remove only the select one or two files, so I cleared the history. Now, the files I view are not being saved to this drop down menu. I have to climb through 4 levels of files to get to the one document I need. How can I get File Explorer (not Windows Explorer) to start saving my recent activity again?

Thank you so much for your quick reply. I'm not really concerned about the start menu. I need these items to show up in the drop down menus in the address bars at the top of the screen. There is a little blue arrow next to the address bar. When I click on that, it should show where I've been before. It used to. It got a little crowded a few months ago, so I right-clicked on it and chose "delete history". The specific address bars are for my libraries. I think I've uploaded a screenshot correctly. As you can see... my drop down menu is blank. It should have my recent activity. If you can tell me how to get this to work correctly, I would truly appreciate it.

I'm sorry... I wasn't clear. The Recent Items does show up in my Start Menu, but they are not showing up in the drop down menus.

Thanks for the reply. Everything was already check under that (except "feeds" - which I have checked now). It didn't seem to make a difference. I opened several documents, but here is still no history showing up in the drop down menus in File Explorer.