Facial expressions are an important component of primate communication that functions to transmit social information and modulate intentions and motivations. Chimpanzees and macaques, for example, produce a variety of facial expressions when communicating with conspecifics. Hylobatids also produce various facial expressions; however, the origin and function of these facial expressions are still largely unclear. It has been suggested that larger facial expression repertoires may have evolved in the context of social complexity, but this link has yet to be tested at a broader empirical basis. The social complexity hypothesis offers a possible explanation for the evolution of complex communicative signals such as facial expressions, because as the complexity of an individual's social environment increases so does the need for communicative signals. We used an intraspecies, pair-focused study design to test the link between facial expressions and sociality within hylobatids, specifically the strength of pair-bonds. The current study compared 206 hr of video and 103 hr of focal animal data for ten hylobatid pairs from three genera (Nomascus, Hoolock, and Hylobates) living at the Gibbon Conservation Center. Using video footage, we explored 5,969 facial expressions along three dimensions: repertoire use, repertoire breadth, and facial expression synchrony [FES]. We then used focal animal data to compare dimensions of facial expressiveness to pair bond strength and behavioral synchrony. Hylobatids in our study overlapped in only half of their facial expressions (50%) with the only other detailed, quantitative study of hylobatid facial expressions, while 27 facial expressions were uniquely observed in our study animals. Taken together, hylobatids have a large facial expression repertoire of at least 80 unique facial expressions. Contrary to our prediction, facial repertoire composition was not significantly correlated with pair bond strength, rates of territorial synchrony, or rates of behavioral synchrony. We found that FES was the strongest measure of hylobatid expressiveness and was significantly positively correlated with higher sociality index scores; however, FES showed no significant correlation with behavioral synchrony. No noticeable differences between pairs were found regarding rates of behavioral or territorial synchrony. Facial repertoire sizes and FES were not significantly correlated with rates of behavioral synchrony or territorial synchrony. Our study confirms an important role of facial expressions in maintaining pair bonds and coordinating activities in hylobatids. Data support the hypothesis that facial expressions and sociality have been linked in hylobatid and primate evolution. It is possible that larger facial repertoires may have contributed to strengthening pair bonds in primates, because richer facial repertoires provide more opportunities for FES which can effectively increase the "understanding" between partners through smoother coordination of interaction patterns. This study supports the social complexity hypothesis as the driving force for the evolution of complex communication signaling.