I call this practice "speedo training wheels". He'll probably lose the shorts once he feels comfortable and confident. The board shorts will become sprinters, then square-cuts and then just the swim briefs (it may stop there, or it may progress into briefer swim wear). It's quite magical to watch this sort of evolution/growth happen right before your eyes.
It's especially rewarding to watch a friend go through this transformation, especially a friend who sorely needs the confidence.
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