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!")

• Elizabeth Shelby's great-great-great-grandmother. (NF novel: Being Human)

• Elizabeth Shelby's great-great-great-grandmother's sister. (NF novel: Being Human)

• Elizabeth Shelby's great-great-grandmother. (NF novel: Being Human)

• 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")

• Janet Wallace, circa 2261: (TOS episode: "The Deadly Years")

• Areel Shaw, circa 2263: (TOS episode: "Court Martial")

• Andrea (android), 2266, Kirk makes advances to confuse her programming: (TOS episode: "What Are Little Girls Made Of?")

• Lenore Karidian: (TOS episode: "The Conscience of the King")

• Helen Noel, 2266: (TOS episode: "Dagger of the Mind")

• Miramanee: (TOS episode: "The Paradise Syndrome")

• Kelinda: (TOS episode: "By Any Other Name")

• Eve McHuron: (TOS episode: "Mudd's Women")

• Marlena Moreau (mirror): (TOS episode: "Mirror, Mirror")

• Nona: (TOS episode: "A Private Little War")

• Shahna: (TOS episode: "The Gamesters of Triskelion")

• Sylvia : (TOS episode: "Catspaw")

• Thalassa, (while using the body of Ann Mulhall): (TOS episode: "Return to Tomorrow")

• Deela: (TOS episode: "Wink of an Eye")

• Elaan: (TOS episode: "Elaan of Troyius")

• Marta, 2269, originally Captain Garth's "Orion girl", she switched loyalties: (TOS episode: "Whom Gods Destroy")

• Gilla Dupree, 2269 (TOS novel: Devil World)

• 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)

• Edith Keeler: (TOS episode: "The City on the Edge of Forever")

• Captain Hunter, Kirk nearly group married her three times prior to 2270. (TOS novel: The Entropy Effect)

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TOS, seasons 1-3 (to be filled in)

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TAS (to be filled in)

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• Lori Ciana, circa 2271: 1-year marriage contract: (TOS novelization Star Trek: The Motion Picture)

• Antonia Salvatori, 2282-2284: (TNG movie Star Trek Generations)

• Gillian Taylor, briefly, in 2286: (TOS movie Star Trek IV: The Voyage Home)

• R.J. Blaise in 2287 and 2290. (DC Comics second series))

• Martia, briefly in 2293: (TOS movie: Star Trek VI: The Undiscovered Country)

• Teilani in 2293 and 2371-2375. (TOS novel The Ashes of Eden)

• Barbara O'Marla in 2294. (TOS novel: The Fearful Summons)