Plants in the Gesneriaceae family are appreciated for their decorative leaves and flowers, ease of cultivation, and shade tolerance. Sexual hybridisation has long been carried out for producing novel hybrids. However, scientific knowledge is lacking on the correct timing of pollination in this family. This study was conducted to elucidate the optimal timing for pollination by screening pollen viability and stigma receptivity throughout the flowering period in eight gesneriad taxa. Pollen viability was evaluated by the in vitro germination test and stigma receptivity was based on stigma morphology and pistil length. The flowering duration varied from 10 days in Alsobia to 18 days in Streptocarpus. While the pollens of Episcia, Kohleria, Saintpaulia, Sinningia, and Smithiantha had totally lost viability 2–5 days before the flowers withered, a slightly contrasting situation was observed in the cases of Alsobia, Deinostigma, and Streptocarpus, where a small portion of pollen grains remained viable towards the end of the flowering period. The highest pollen germination rate was recorded from 1 day in Alsobia, Episcia, and Kohleria, to 9 days in Deinostigma. The reduction in pollen germination was rapid in Alsobia, Saintpaulia, and Smithiantha, and moderate in the remaining taxa. The greatest pollen tube growth occurred at 1–3 days after flower opening and decreased rapidly in all the taxa tested. The longest pistil of 2.03–3.50 cm was observed at 3–8 days of anthesis depending on the plant tested. The findings in this study suggest that higher pollination success may be achieved using pollen grains of newly opened flowers and stigmas of mature flowers in this family.