Problem: Sentence1: He borrowed a large sum.
Sentence2: A tidy sum.
Q: Does the term sum mean the same thing in both these sentences?

Answer: the same meaning

Problem: Sentence1: He tries to hit on women in bars.
Sentence2: He hit a home run.
Q: Does the term hit mean the same thing in both these sentences?

Answer: different meanings

Problem: Sentence1: The French doors admit onto the yard.
Sentence2: This pipe admits air.
Q: Does the term admit mean the same thing in both these sentences?

Answer: different meanings

Problem: Sentence1: I'll hold you by your promise.
Sentence2: He's held by a contract.
Q: Does the term hold mean the same thing in both these sentences?

Answer:
the same meaning