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As someone who actually more recently became a Pearlshipper and who's watched All seasons of DP twice over now. I'll just say this:
This ship only works if you take the angle of "time apart makes the heart grow fonder" Dawn and Ash were really good friends to the point of acting like siblings. Probably the closest relationship he had with any of the girls in the series. But there really isn't much of anything to go on between them, and Ash was written at peak density at that time as well, something that they alleviated to some extent in XY given some of his behavior - though not too much - to Serena.
This stuff is better left to fanfics.