The performance of plant hybrids relative to line breeding types is generally associated with higher yields, better adaptation, and improved yield stability. In bread wheat (Triticum aestivum L.), however, a broad commercial success for hybrids has not been accomplished until now largely due to the low efficiency of hybrid grain production, which is highly attributable to its self-pollinating nature. To better understand how hybrid wheat grains can be produced more effectively, we investigated the influence of synchronized flowering between female, i.e. male-sterile, lines and their male cross-pollinator lines as well as of the duration of flowering on hybrid grain production. We found that synchronization of flowering in combination with the longest possible temporal overlap had the largest positive effect on hybrid grain production. However, despite sufficient spatial and temporal synchronization of flowering, we also found that some female lines had lower hybrid grain set than others, suggesting genetic differences in female floral receptivity. To better assess female receptivity, we established a new phenotyping scale of male-sterile wheat flowers that provides the floral basics for effective cross-pollination. Applying this scale in our field and greenhouse trials revealed that better performing female lines remained longer in the pollen-receptive phase.