James T. Kirk/Relationships/Romances/2250s/Janice Lester

Kirk had a year-long relationship with Janice Lester while she also was at the Academy. He professed loving her, but the romance ended badly after "the intense hatred of her own womanhood made life with her impossible." The two were reunited in a truly bizarre manner in 2269, when Lester, extremely jealous of Kirk's successful career, traded her consciousness with that of Kirk's to take his place as captain of the Enterprise and then exact a double revenge by killing both Kirk and her womanhood. ()
In the late 2250s, as an instructor at the Academy, Lieutenant Kirk was romantically involved with a "blonde lab technician" whom Gary Mitchell had introduced him to. His relationship with her grew serious, as he almost married her. ()