I have ALWAYS taken Lester's comment "Your world of Starship Captains doesn't allow women" as Kirk's obsession with becoming a Captain left no room for her, not that female Captains are not allowed.
That's how I've always seen it.

I have ALWAYS taken Lester's comment "Your world of Starship Captains doesn't allow women" as Kirk's obsession with becoming a Captain left no room for her, not that female Captains are not allowed.
As others have said....at the time I think it meant women weren't allowed to be captains. It was made in the 1960s...over years Retconned over the years to say she washed out due to her own issues and that she thinks kirk dumped her for starfleet instead
It is worth noting that although Roddenberry's story outline is full of sexism, that particular line doesn't show up until the teleplay, which he didn't write.
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