There is no other way to put this: essentially everything about Popular Consciousness Kirk is bullshit. Kirk, as received through mass culture memory and reflected in its productive imaginary (and subsequent franchise output, including the reboot movies), has little or no basis in Shatner's performance and the television show as aired. Macho, brash Kirk is a mass hallucination.
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With the exception of Lester, all Kirk's relationships that we're aware of seem to have ended amicably. He and the women involved have often kept up communication to some extent, despite the impediments caused by interstellar travel (Wallace, Marcus). The relationships all seem to have been of some duration, and characterised by fairly serious involvement on both parts. They were distinctly emotional affairs, and no one accuses Kirk of having "womanised" during them. They all involved competent people drawn to demanding, intellectually stimulating fields—usually science—and the service of something greater than themselves—almost universally Starfleet.
Kirk's storied history of womanising seemingly consists of his having seriously dated a fairly small number of clever women in Uni. We're even told Kirk had to be manipulated into paying attention to matters of the heart and/or loins during that period (and that Kirk's into "longhair stuff" like 17th-century philosophy)
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Kirk does have an occasional one-episode romance arc with a woman (Edith Keeler is the most notable entry in this category). There are a handful of such moments across three American-length seasons, which actually adds up to significantly less romancing than most contemporary television characters on equivalent programs are expected to get up to. J. D. from Scrubs
has more flings. This list doesn't even count the textual crushes (I hate this show; my girlfriend doesn't). Seriously, board games I'm selling because I don't like them enough see more play than Kirk. He's just too into his work.
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Face it: Kirk is a big nerd who punches people sometimes, but also memorises poetry and has nice chats with Spock's mom and loves the ship intensely. He's less tasked with enacting toxic masculinity in all its forms than many a contemporary male lead. He's a great protagonist: simply enjoyable to watch, effective and interesting in his setting, and more complex and lovely than he's given credit for. Kirk's as good a character as Spock: that's how their dynamic and show work. I would swap any one of thirty contemporary white-dude-show-leads for Kirk in a damn heartbeat.
