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- This page is a comprehensive (and as much as possible, chronological) compilation of the women with whom James T. Kirk has had romantic entanglements (even briefly)."
- "a new girl every week" in high school: (TOS novel: Best Destiny)
- Emily (surname unspecified), 2249: (Best Destiny)
- Ruth (surname unspecified), just before beginning at Starfleet Academy: (TOS episode: "Shore Leave"; TOS comic: "Starfleet Academy!")
- Unnamed blond lab technician, while at Starfleet Academy. Nearly married her: (TOS episode: "Where No Man Has Gone Before")
- It is possible that Carol Marcus and the blond lab technician are the same person.
- Janice Lester, at Academy or early, Starfleet career (mid-2250s): (TOS episode: "Turnabout Intruder")
- Carol Marcus, circa 2254 to 2260, gave birth to David Marcus in 2261: (TOS movie: Star Trek II: The Wrath of Khan; TOS comic: "Star-Crossed")
- Andrea (android), 2266, Kirk makes advances to confuse her programming: (TOS episode: "What Are Little Girls Made Of?")
- Marta, 2269, originally Captain Garth's "Orion girl", she switched loyalties: (TOS episode: "Whom Gods Destroy")
- Miranda Jones, Kirk's charm in the end impressed her and gave her flowers before she left. (TOS episode: "Is There in Truth No Beauty?")
- Rayna Kapec (android), 2269, Kirk made advances-unintentionally confusing her programming: (TOS episode: "Requiem for Methuselah")
- Ola, a small, fury, naked creature from Lyra. In 2269, she was married to Kirk without his consent. (TOS novel: The Starless World)
- Captain Hunter, Kirk nearly group married her three times prior to 2270. (TOS novel: The Entropy Effect)
TOS, seasons 1-3 (to be filled in)
TAS (to be filled in)