Ok here we go with a list of the women that Kirk loved!
Ruth (surname unspecified), just before beginning at Starfleet Academy: (TOS episode: "Shore Leave")
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)
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")
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")
Edith Keeler: (TOS episode: "The City on the Edge of Forever")
Since I ripped this off from Memory Beta I should give the link.
memory-beta.wikia.com/wiki/Kirk's_women
