Cryptic crossword clue
Watching man following someone he knew at school? 9

The most common and most likely answer to this crossword clue is the 9 letter word OBSERVANT

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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.
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What does OBSERVANT mean?

OBSERVANT adjective
  1. Alert and paying close attention; watchful.
  2. Diligently attentive in observing a law, custom, duty or principle; regardful; mindful.

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