Something that maybe should be considered here: Perhaps there's cultural differences at play here?
A guy in his mid-to-late teens having dated 3 or 4 girls over a few years is not especially noteworthy in modern America... but maybe it is in modern Japan? I'm not Japanese, so I wouldn't know.
So maybe from Shouma's cultural perspective, a guy that does that is a bit of a playboy. In other words, the very term "playboy" has meanings relative to the culture it's used within.
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