If you restrict the idea to 'if' and 'while', Why not render this using the existing 'as' form for binding names, already used with 'except' and 'with':

while learner.get(static_hint) as points:

learner.feed(f(points))

The equivalent for 'if' helps with the regex matching case:

if re.match(r"...") as m:

print(m.group(1))

I considered proposing these two forms in a PEP a few years ago, but never got around to it. To my eye, they fit syntactically into the language as-is, without introducing new symbols, operators or keywords, are consistent with existing usage, and address two relatively common causes of displeasing Python code.

Robert