The use of filters and editing tools for perfecting selfies is increasing. While some aesthetic experts have touted the ability of this technology to help patients convey their aesthetic goals, others have expressed concerns about the unrealistic expectations that may come from the ability for individuals to digitally alter their own photos in these so-called “super-selfies.” The aim of the study is to determine the changes that individuals seek when enhancing selfies. Twenty subjects participated in this study between July 25 and September 24, 2019. Subjects had two sets of headshots taken (neutral and smile) and were provided an introduction on the use of the Facetune2 app. Subjects received a digital copy of their photographs and were asked to download the free mobile app. After 1 week of trialing the different tools for enhancing their appearance, subjects submitted their self-determined most attractive edited photographs. Changes in marginal reflex distance (MRD) 1 and 2, nose height and width, eyebrow height, facial width, skin smoothness, skin hue, and saturation as well as overall image brightness were recorded. Paired two-tailed t-test was used to evaluate pre- and post-facial measurements. There were no statistically significant changes identified in the analysis of the altered photos in neutral expression. Analysis of all smiling photographs revealed that subjects increased their smile angle (right: +2.92 mm, p = 0.04; left: +3.58 mm, p < 0.001). When smiling photographs were assessed by gender, females were found to significantly increase their MRD2 (right: +0.64 mm, p = 0.04; left: +0.74 mm, p = 0.05) and their smile angle (right: +1.90 mm, p = 0.03; left: +2.31 mm, p = 0.005) while also decreasing their nose height (−2.8 mm, p = 0.04). Males did not significantly alter any of the facial measurements assessed. This study identifies the types of changes that individuals seek when enhancing selfies and specifies the different aspects of image adjustment that may be sought based on a patient's gender.