It’s also important to bear in mind that the Original Series had a predominantly female fanbase, and during its initial run, was widely mocked and dismissed by mainstream (i.e., male) science fiction fans as being fake sci-fi for girls. It’s difficult to overstate the influence women had on the franchise in its early days; most of the early Star Trek conventions were organised by and for women, and indeed, those same organisers were primarily responsible for the massive letter-writing campaign that prevented the show from being cancelled after the 1968 season. Without that campaign, the episode pictured in this post would never have been made.
The popular image of James Kirk as a sleazy womaniser is part of a conscious effort to erase that history and render the franchise’s roots palatable to the misogynistic geekboys of the modern SF/F fandom.