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This study investigates the collocational patterns and semantic imports of past perfect subjunctive conditionals in conversational English by analyzing data extracted from the Brown University Corpus and the Kaggle Blog Authorship Corpus. The analysis focuses on identifying common forms of collocations and connotations that the conditionals accompany or constitute. The findings show that past perfect subjunctive conditionals are used to express a range of emotions and cognitive appraisals, with expressions of more desirable situations and speculative comments on event causality being the most prevalent. Formal features, such as the addition of an adversative but-clause, main clauses in interrogative mood, and the denotation of specific time points, alongside semantic features such as sharing of emotions, discordance between actual-epistemic and ideal-deontic states of being, and perlocutionary effects like humor and sarcasm, demonstrate the unique communicative and discourse functions of past perfect subjunctive conditionals. The study offers practical insights for learners of English and suggests that input materials reflecting the functional underpinnings of the past perfect subjunctive conditional can enhance their understanding and productive use of the structure.