Not sure if you got this resolved, but I had what appeared to be a similar issue.
Displaying the current date from python was not working, then suddenly it worked. Reason is that I am in Australia so pythonanywhere's current date is different to my local time.
The only way to resolve this was to use javascript.
In the base.html template file (at the end) put a function to setup where you want your date
<script>
var elem = document.getElementById("timeNow")
var now = new Date();
var options = { format: 'DMY', weekday: 'long', year: 'numeric', month: 'long', day: '2-digit' };
elem.innerHTML = now.toLocaleString('en-au', options);
</script>
Then on the page you want it displayed, add that element "timeNow"
e.g. on my calendar page
<span id="timeNow"></span>
This works fine, but if there is a cleaner (non javascript) way that anyone has used, I'd love to know about.
Cheers,
Duncan