I’m not entirely sure what you were trying to demonstrate, but clearly the result of datetime.now() changes between the two invocations (it has microsecond precision).
Try:
>>> from datetime import datetime, timedelta
>>> now = datetime.now()
>>> now - (now + timedelta(days=1))
datetime.timedelta(-1)
datetime.timedelta internally uses a triple of (days,seconds,microseconds) to represent it's data and exposes that to users of the class.
That a timedelta can be represented in multiple ways is alone quite surprising but some of the representations that happen can be very confusing. I think the example I gave which represents "-1 day and a few microseconds" as "-2 days + 86399 milliseconds + 999969 microseconds" is very surprising and it commonly happens in practice.
Try: