Most “seedless” fruits are not, in fact, actually seedless. In the classical example of the Watermelon, you can actually see this–most will have little white seed husks that you can find where the seeds would normally be, that are edible and you can eat along with the flesh largely without noticing. In this and most cases of seedless fruits, what they actually are is under-ripe–strains that have been cultivated to be tasty earlier in the development of the fruit, and put resources into developing seeds later on, so the grower can harvest some plants early as “seedless” variants, and then later harvest the normal crop and use seeds from those fully developed fruits to plant the next generation.
Trees, interestingly, are the one place where this can actually be not the case (although it often still is): most fruit trees are clones of single individuals, grown from cuttings of the original tree and propagated that way. Since they’re rarely grown from seed (and in fact doing so is unlikely to result in a fruit as good as the one the tree you have has), you can have a continuing population of “seedless” fruits from a tree because, basically, humans are circumventing the natural reproduction mechanism entirely. I’m not aware of any situations where this is the case off hand, but it wouldn’t surprise me if they exist. I know there’s cases, for example, where some tree strains actually have to be grafted onto different strains of tree because the genetics they have for trunk development will not support the amount and volume of branches and fruit the tree is able to produce.
Actual ELI5: most seedless fruit is just under-ripe fruit, not from a seedless fruit plant.
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