Hi JRice.Protingent
Thanks for posting the thread on our forum.
As per your description, please don’t worry we can work together to narrow down and resolve the situation.
Based on your description, it seems that you want to the events can display both two dates you set in the event page.
We did a test on our end, it just display the firs date in the description as yours
To meet your requirements, we suggest you go to site contents>Events>the select the event you created>Edit event>check the Recurrence box: Make this a repeating event.
Then in the display page, in the Recurrence option, select how do you want the event recur>you can select weekly, monthly and so on.>Click Ok.
Then you can see the result as the screenshot below(I select weekly)
Here is a similar scenario like yours, you can have a reference: sharepoint online - Show recurring events in the new Event Web Part - SharePoint Stack Exchange
Meanwhile, I want to confirm some information with you:
Can you provide the whole screenshot of the image with your events you provided?
Hope the suggestion can help you .
Regards,
Stacey