We meet "Rayna Kapec" in Requiem For Methuselah. She seemed like the ideal woman to Jim Kirk. She had the rare quality that he most admires in a woman: she was brainier than Stephen Hawkings.
Kirk fell instantly in love with her. Too bad she was just an exquisitely well-fashioned android. Well, by the time Kirk realized she was a mechanical doll, he was already head-over-heels and not thinking straight. She was so real, so believable, that he couldn't help but hand his heart directly over to her.
Interestingly, she "loved" Kirk in return. She is an early example of a nearly sentient android, predating TNG's Data by a good stretch of years.
Her creator Flint had created her to be his own companion, so he was not pleased when he realized that "Rayna's" slumbering emotional potential had just been awakened by another man.
Jim and Flint begin to fight over "her", but "she" called a halt to it.
Rayna: "Stop! I choose where I want to go, what I want to do! I CHOOSE!"
Kirk rejoiced at this. Was she sentient? Kirk obviously thought she was.
Kirk: "Rayna belongs to herself, and she claims the human right of choice... to be as she wills, to do as she wills, to think as she wills!"
So the men stop fighting and agree to allow the android to choose between them, but the choice was too perplexing for "her", and it fried her circuits.
[Probably because she couldn't figure out a nice way to tell them that she wanted more choices, HA!]
Kirk said and did many wildly irrational things in this episode presumably because his judgment was effected by strong emotion. Just because Kirk pronounced her to be human doesn't mean that she was human.
The truth is that Flint created Rayna, and he did own her, and she was nothing but a highly sophisticated machine that couldn't take the strain of being self-aware, and self-directing... but she sure gave it a good try. Dang, that was close!
Many people like to point to this anomalous affair as evidence that Kirk is a raging heterosexual, but they forget that this episode has a most bizarre and controversial ending. At the end, Spock sneaks up on a sleeping Kirk, melds with him, and telepathically causes him to forget Rayna Kapec.
WHAT is UP with THAT!? That is the sort of thing that fuels the speculation about the true nature of the Kirk/Spock relationship.
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