If I am not sure how to distinguish among the connotations of words with similar denotations, one strategy I can use is

to look up the words in a thesaurus to see synonyms with different connotations. Additionally, I can read the words in different contexts to see how they are used and pick up on subtle differences in meaning. I can also consult with a teacher, tutor, or language expert for guidance on the nuances between the words in question.

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Another strategy I can use is to pay close attention to the specific context in which the words are being used. Words can have different connotations depending on the setting, audience, and tone of the communication. By analyzing how the words are used in a sentence or paragraph, I may be able to discern the subtle differences in connotation.

I can also consider the historical or cultural associations of the words. Words may have accrued certain connotations over time based on their usage in literature, media, or popular culture. By exploring the origins and cultural contexts of the words, I may gain a deeper understanding of their nuanced connotations.

Furthermore, I can practice using the words in my own writing or speaking to see how they feel and sound in different contexts. Experimenting with the words in various sentences or situations can help me to grasp their shades of meaning and connotation more effectively.

Overall, by utilizing a combination of these strategies - such as consulting a thesaurus, analyzing context, exploring historical/cultural associations, and practicing usage - I can enhance my ability to distinguish among words with similar denotations but different connotations.