‘WA 38’ (‘Enterprise’ × ‘Honeycrisp’) is an apple variety that is characterized by a peculiar self-thinning trait in which most of the fruitlets naturally shed within the first 8 weeks after bloom, leaving some clusters empty, but most with 1–2 apples. This study aimed to investigate potential causes for the relatively low fruit set observed in ‘WA 38’ by investigating its flower biology. This study comprised three objectives: (1) To characterize the effective pollination period (EPP) of ‘WA 38’ by studying stigmatic receptivity, pollen tube growth, and ovule longevity in ‘WA 38’ flowers, (2) to compare the pollen tube growth of 5 fully compatible pollinizer varieties in ‘WA 38’ pistils, and (3) to evaluate fruit and seed set resulting from controlled pollinations with 5 fully compatible pollinizer varieties. The results showed ‘WA 38’ EPP was approximately 3.2 days in 2019 and 1.4 days in 2020, and that differences in pollen sources did not attribute significant differences in fertility in ‘WA 38’ flowers. The results of this study suggest mechanisms other than pollination and fertilization, such as competition among fruitlets within a cluster or hormone signaling, may have a stronger impact on ‘WA 38’ fruitlet abscission.