I was thinking about Odona from "The Mark of Gideon," because while she's not the most compelling of the women of the week by any means (or even of the ones in Kirkmances specifically), she is the most ambiguous in some ways and I find it interesting.
This is the episode in which he essentially tells pro-life death cultists that they should take responsibility for their own dicks and use contraception, and is both baffled at their refusal to do so and enraged that they find it morally superior to sacrifice the life of an actual living woman than to use contraception because sanctity of the fetus blahblahblah.
The actual living woman in question is Odona; she's essentially sent by her people (the pro-life death cult folk dealing with immense overpopulation) to romance Kirk in order to get close enough to steal his blood. The sole reason he's chosen is because he nearly died of meningitis once and they can use his infected blood to basically reinvent death.
Obviously, isolating, confusing, lying to, and seducing someone in order to non-consensually steal his blood to kill people with is ... uh, problematic. Odona is unusual among the TOS female characters who make major missteps around consent, though, because she knows it's wrong all along and she actually feels terrible about it. But she's been chosen to bring the sweet release of death to her people and her loyalty to them supersedes her guilt over using Kirk.
By the end, Odona and Kirk still like each other pretty well—not on the level of Kirk/Areel or Kirk/Edith, but enough that she tries to convince him to stay, he tries to convince her to leave the pro-life assholes behind, and both gracefully accept their failures to convince the other.
But there's this interesting exchange in their final interaction, in which Odona tells Kirk that she knew lying and using him the way she did was wrong, she believes he has every right to hate her for it, and she appreciates that he's being so gracious and gentlemanly about the whole thing. Kirk seems clearly quite touched by this, even though it's not unusual for him to respond to some fundamental violation by extricating himself in a gentle and flattering way before noping out.
I think it's significant to this that Kirk typically tries to soften the blow this way in the more purely "wtf?!" situations or people he deals with (at least when the context is more or less sexual). That's not exceptional. The part that's really unusual is Odona's response. She doesn't try to righteously challenge the flattery, or downplay the violation of his basic right to his own bodily autonomy. She just accepts the compliment for what it is (and no more), and acknowledges that he's being a lot more understanding and charming about the whole thing than anyone could expect of him.
In a way, someone who wrongs another person in this regard just admitting, "hey, I know this was fucked-up and I appreciate that you're being so pleasant about it when you owe me less than nothing" seems like a very low bar. But it doesn't happen much in TOS, especially not to Kirk, someone whose rights as a person to basic decency have been repeatedly violated since childhood, often with those responsible refusing to admit to wrongdoing, much less face consequences. I get the impression that Odona's simple acknowledgment that the people of Gideon wronged him and he's being really nice about it means a lot to him—not only because it's coming from Odona, but because it's being acknowledged at all.
I had another TOS poll in the queue for when some big ones wrapped up, though this one is less about my intense Kirk/Spock shipping and more about Feelings About My Blorbo Specifically.
So, TOS Kirk has a lot of relationships with women that I find really compelling (in a positive way!) for some reason or another, out of all proportion to their screen time, based entirely on what we're told/shown in the original series itself. Pick which one of these relationships speaks to you the most!
Which of these relationships between James Kirk and women do you most care about?
Kirk & Aurelan
Kirk & Uhura
Kirk & Areel
Kirk (Prime) & Marlena
Kirk & Amanda
Kirk & unnamed reliable female friends
Kirk & the pretty yeomen Starfleet keeps assigning to him
Kirk & T'Pau
Kirk & Odona
Voting ended onNov 14, 2025
The only reminders for this one: I excluded the people I did for a reason, and it's all about Kirk in the show, not the various movie versions of Kirk or SNW or whatever. If you don't remember all of these relationships, some summations:
1— Aurelan is Kirk's sister-in-law, who he's on close, affectionate terms with; she showed up to celebrate his professional achievements, and he grieves her death after his brother Sam's in "Operation: Annihilate!"
2— Kirk and Uhura have a lot of intense platonic affection and respect for each other throughout the entire show. It's filtered through their strict professionalism and mutual presentations of soothing layers of composure and hypercompetence over their high-strung, anxious personalities, but below the surface they're clearly good friends.
3— Areel is Kirk's amicable ex and long-time friend in "Court Martial" (played by an actress the same age as William Shatner), and both adheres to her professional ethics as prosecutor and remains a staunch friend, by direct contrast to the unreliability of nearly all his once-friendly long-time male acquaintances in Starfleet.
4— Marlena Moreau is "the captain's woman" in the Mirror Universe from "Mirror, Mirror." Kirk is visibly uncomfortable with having to play along, but they like each other for real, and he tries to convince her to follow her own ambitions before deciding to befriend her prime counterpart.
5— Amanda is Spock's mother; she and Kirk get on like a house on fire when they meet at last in "Journey to Babel."
6— In "Court Martial," McCoy remarks that, apart from himself, Kirk's real "old friends" exclusively "look like Areel" (an attractive woman Kirk's age) whereas his own are doctors (implicitly aging male doctors like himself). McCoy earlier joked in "The Man Trap" that Kirk's affinity for flowers is why he gets on well with women.
7— Kirk has mutually strong rapport with his invariably female yeomen: they're loyal and concerned, even ones who aren't remotely attracted to him, and he treats them carefully.
8— T'Pau is one of the most prestigious people on Vulcan (and probably the entire Federation), and in "Amok Time," Kirk is revealed to be a massive fanboy of hers and she saves his career.
9— Odona is a young woman sent to acquire Kirk's blood (he once nearly died of meningitis) to bring death to her miserably immortal people in "The Mark of Gideon." She flirts with him to get near enough, but they genuinely like each other, (very unusually) she actually apologizes for the dubcon, and they respect each other's autonomy otherwise.
