This corpus-based study investigates the similarities and differences among the three synonymous adjectives: "careful," "cautious," and "wary" in terms of genre distribution, collocational patterns, semantic preference, and semantic prosody. Data were drawn from the Corpus of Contemporary American English (COCA). The results reveal that "careful" occurs widely across both formal and informal genres, with the highest frequency in TV and movie subtitles. In contrast, "cautious" and "wary" are predominantly found in more formal genres, such as newspapers and academic text. Collocational patterns further distinguish that "careful" frequently co-occurs with nouns such as "attention," "consideration," "analysis," "planning," and "examination." "Cautious" commonly collocates with "approach," "optimism," "step," "investor," and "consumer." Wary tends to appear with nouns such as "eye," "investor," "look," "consumer," and "glance." While "cautious" and "wary" share several collocates and semantic preferences, "careful" does not overlap significantly with either. The majority of noun collocates with "careful" fall under the theme reflecting cognitive or analytical processes. Most noun collocates of "cautious" tend to appear in financial or economic contexts, while those of "wary" primarily relate to people and social perception. In terms of semantic prosody, "careful" exhibits neutral tones, whereas "cautious" exhibits neutral to negative prosody and "wary" is generally associated with a more negative connotation. These findings demonstrate that, despite their synonymous definitions, "careful," "cautious," and "wary" are not fully interchangeable across contexts due to distinct linguistic and semantic patterns.