Background: Ankyloglossia (tongue tie) is a condition of limited tongue mobility caused by a restrictive lingual frenulum, often considered a factor that can affect oral motor function and development. The present study aimed to explore associations between certain skeletal and dental characteristics in adolescents and partial ankyloglossia. Methods: The following data were collected from 100 subjects (53%male, mean age 15.7 ± 2.9 years): general demographic information (e.g., history of breastfeeding, use of a pacifier, past tonsillectomy, mouth breathing, snoring, sleep and/or awake bruxism and other), clinical evaluation (including maximal mouth opening, the shape of profile, free tongue measurement), and evaluation of dental and skeletal characteristics (measured on dental study models and cephalograms). The degree of ankyloglossia was evaluated through free tongue measurement. Results: Both maxillary inter-molar wide/length proportion and Frankfurt mandibular plane angle (FMA) can significantly predict tongue mobility (free tongue measurement). For a one-unit increase in the maxillary inter-molar wide/length proportion, there was a decrease of about 6.3 millimeters in the free tongue measurement. For each degree in FMA, free tongue measurement increased by about 0.2 millimeters. Conclusions: Results failed to present strong evidence to support a direct association between the severity of ankyloglossia and various skeletal and occlusal characteristics. Maxilla development is complex and multifactorial, including factors such as free tongue length, tongue mobility, and other oral functions, tongue tie being only one piece of the puzzle.