The most common and most likely answer to this crossword clue is the 7 plus 7 letter word SQUARES CIRCLES
I've seen this crossword clue in The Guardian
S
Q
U
A
R
E
S
C
I
R
C
L
E
S
Buddy explains!
The straight part
We know that "repeatedly does the impossible?" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case repeatedly does the impossible? = squares circles.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.