Using older versions of Outlook for Mac for personal email and calendar
The issue persists for me using Legacy Outlook for Mac. I have tried the New Outlook but it's missing key features I depend on at work.
Hopefully they will take note of this Unicode malfunction and fix it! It's like it has to unravel the emoji language each time Outlook is newly opened and it encounters an emoji. Once you get thru one, it seems ok. Unless you restart, then it reoccurs.