I stumbled upon a possible bug in the Python interpreter while doing some Python version comparisons.

Look at this:
"3.10.2" < "3.8.2"
True  # This is not true as a version number comparison

Now look at this:
"3.10.2" < "3.08.2"
False  # Adding a leading 0 compares those two version numbers correctly

Is it possible Python is fixed to correctly compare such numbers? That would make comparing Python version numbers possible in the future.

import platform
if platform.python_version() < "3.8.2":
    # Do something

This is currently possible and correct, but this will break when Python version number becomes 3.10 and you wanna compare this version number to, say, 3.9.

That's why for over a decade we've been recommending not to use string comparisons to compare versions. You have to parse the version and then compare the numeric values.

What is then the most Pythonic way of comparing two version numbers?

That's a question for a user forum. There's some code in Lib/distutils/version.py.