Cryptic crossword clue
Habitual pretender: old-maidish and head of school in addition 6

The most common and most likely answer to this crossword clue is the 6 letter word POSSUM

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Buddy explains!

The straight part
We know that "Habitual pretender" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case habitual pretender = possum.
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.

What does POSSUM mean?

POSSUM noun
  1. An opossum, a marsupial of the family Didelphidae of the Americas.
  2. Any of the marsupials in several families of the order Diprotodontia of Australia and neighboring islands.

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