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The quality of children’s relationships with teachers in early elementary grades has implications for their academic and behavioral outcomes in later grades (e.g., Hamre & Pianta, 2001). The current study uses data from the NICHD SECCYD to extend work from a recent study of first grade (Rudasill & Rimm-Kaufman, 2009) by examining connections between child shyness, effortful control, and gender and teacher–child relationship quality in third grade directly and indirectly through the frequency of teacher- and child-initiated interactions in third grade, and teacher–child relationship quality in first grade. Path analyses using structural equation models were used to test two different models, one for conflict and one for closeness. Findings reveal five main points: (a) Children’s characteristics (i.e., shyness and effortful control) were related to the frequency of interactions they initiated with their third grade teachers; (b) The number of teacher-initiated interactions with a child in third grade was positively related to teacher perception of conflict, but not closeness, with that child; (c) Teachers’ perceptions of relationship quality and the number of teacher-initiated interactions in first grade predicted teachers’ perceptions of relationship quality and the number of teacher-initiated interactions in third grade; (d) Children’s gender predicted the number of teacher-initiated interactions and teachers’ perceptions of relationship quality in third grade; (e) Teacher–child relationship quality in first grade, and the number of teacher and child-initiated interactions in third grade, mediated associations between children’s characteristics and teacher–child relationship quality in third grade. Findings have implications for future research and training for preservice and practicing teachers.