@Hi @Ethan_Schneider 
thank you for reaching out!
As it stands, the calendar sync is one-way: updates to your calendar will not be reflected in Asana. You can learn more about it in this handy article: Sync Asana + Google Calendar, Outlook, Apple | Product guide • Asana Product Guide
There is an existing thread in the Forum regarding this topic: Real time, two ways Calendar integration. If you haven’t yet, I would encourage to upvote it.
With that said, I would also recommend you to have a look at these 3 third-party integrations:
- https://asana.com/apps/project-buddy
- https://asana.com/apps/skedpal
- https://office.reddiapps.com/processes/asana/googlecalendar
Hope this helps! Please let us know if you have any follow-up questions!