Background/Aim: This pilot study was designed to determine if adolescents had mastered the grammar of past tense counterfactual (PTCF) sentences (e.g., “If Julie had done all of the track workouts, she might have won the state meet”). Of interest was their ability to use the modal, auxiliary, and past participle verbs correctly in the main clause of a PTCF sentence. Prior research had indicated that PTCF sentences were challenging to older children. Hence, we wished to determine if PTCF sentences would continue to challenge adolescents. Methods: The participants were two groups of adolescents, who were aged 13 and 16 years, and a control group of young adults having a mean age of 22 years (n = 40 per group). Each participant read a set of four fables and completed a PTCF sentence based on the story. Each incomplete sentence contained a subordinate clause that employed the past perfect verb form (e.g., “If the fox had been able to jump higher…”). The participant’s task was to complete the sentence in writing, generating a grammatically correct main clause that contained the present perfect verb form (e.g., “he would have been able to reach the delicious grapes.”). Results: On the PTCF sentences task, the 16-year-olds earned a higher mean raw score than the 13-year-olds, but the two groups did not show a statistically significant difference. However, the 22-year-olds performed significantly better than the 13-year-olds. It was also found that using the correct form of the past participle verb was the most difficult aspect of the task for all three groups, and that mastering the grammar of PTCF sentences continued into adulthood. Discussion/Conclusion: The PTCF sentence is a late linguistic attainment, perhaps due to its infrequent occurrence in spoken language. The study offers implications for the concept of grammatical mastery and for the distinction between prescriptive and descriptive grammar.

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