Examine your watermelon vines and note when they start producing female flowers, which are closer to the vine and larger than male flowers, with immature fruit forming at the flower base. The first flowers to develop and bloom on vines are male flowers, which guarantees that pollen is readily available for fertilization.
Pollinate in the morning when flowers are open. Choose a humid day, if possible; mornings are typically the most humid part of the day. Humidity helps activate pollen.
Choose one or more mature male flowers. When you touch the stamen inside each flower, the tiny yellow pollen grains should easily brush off onto your hand. Cut back the petals of the male flowers, so the stamen is fully available.
Select mature female flowers, those that have just opened that morning; female flowers are receptive to fertilization for just one day.
Brush male flower pollen onto the stigma of female flowers, located in the center, with a small paintbrush. Make sure that pollen covers all stigma sections, for fully formed fruit. Watermelons of successfully pollinated flowers will quickly begin growing, noticeable within a week. If pollination fails, immature fruit will shrivel and dry up.