High temperatures (HTs) and high vapor pressure deficits (VPDs) have significant impacts on maize yields, partly due to the high sensitivity of maize tassels. However, there are few studies quantifying the impacts of HTs and VPDs on maize tassel performance under changing environments. Therefore, we carried out a two-year field experiment that included 20 inbred lines and four sowing dates. Compared with the first sowing date, the seed set in the second sowing date decreased by ~80% in both years. The opened spikelet ratio (OSR) and pollen viability (PV) were the key determinants of seed set, and their respective correlation coefficients with seed set were 0.58 and 0.90. The OSR and PV decreased by ~20% and ~50%, respectively, under high-temperature stress. When Tmax exceeded 32.5 °C or the VPD exceeded 0.91 KPa, PV began to decline; when Tmax exceeded 33.8 °C or VPD exceeded 1.10 KPa, the OSR began to decline. The OSR was more dependent on genotypic background than PV (28.4% vs. 19.7%). The maize tassel water content was significantly correlated with the OSR and PV. Based on the OSR and PV values, the 20 genotypes were divided into three different groups, namely the high H, middle M, and low L groups. The H group, on average, had the highest kernel number per ear and seed set, followed by the M and L groups. The average seed sets of the H, M, and L genotypes under the second sowing date were 17.4%, 10.9%, and 0%, respectively, in 2019 and 13.8%, 7.9%, and 0.6%, respectively, in 2020. The present results indicate that selecting maize varieties with a high OSR is an effective approach for improving maize yield under heat stress.