Problem: Sentence1: He wrote a letter of apology to the hostess.
Sentence2: The CEO made a public apology for the scandal, and promised full cooperation with the authorities.
Q: Does the term apology mean the same thing in both these sentences?

Answer: the same meaning

Problem: Sentence1: She knows how to work the system.
Sentence2: He works his parents for sympathy.
Q: Does the term work mean the same thing in both these sentences?

Answer: the same meaning

Problem: Sentence1: The pursuit of love.
Sentence2: Unremitting pursuit of wealth doesn't bring happiness, particularly if successful.
Q: Does the term pursuit mean the same thing in both these sentences?

Answer: different meanings

Problem: Sentence1: He determined the length of the shortest line segment joining the two points.
Sentence2: A length of tubing.
Q: Does the term length mean the same thing in both these sentences?

Answer:
different meanings