James T. Kirk/Relationships/Friendships/Janice Rand

Starfleet assigned Janice Rand as Kirk's personal yeoman in 2266. Initially, he complained about the idea of a female yeoman, leading McCoy to ask flatly, "What's the matter, Jim? Don't you trust yourself?" Kirk said he already had a female to worry about, and that the Enterprise was that female. Kirk warmed to Rand, but an undercurrent of sexual attraction between the two became obvious in stressful situations. Suffering from polywater intoxication in 2266, Kirk confided his attraction for Rand to Spock, shouting that he had "a beautiful yeoman!" Kirk later reached out to her hesitantly, longing for her, but he could not approach her on account of his duty. ()
A transporter malfunction created a duplicate of the captain that contained his negative qualities, such as hostility, lust, and violence. That version of Kirk was consumed with lust and desire for Rand and went "on the prowl" to find her. Eventually, when they both were alone in her quarters, he slowly approached her. Besides being a little startled by his presence, it looked and felt normal for her, until she noticed the captain drinking from a bottle of Saurian brandy. 
Obviously drunk, he started telling her that she was "too beautiful to ignore" and "too much woman." As he stalked closer to her, he claimed that they'd both been "pretending too long." Then, he suddenly grabbed her and began kissing her fiercely. The Kirk duplicate tried to pin her to the floor to rape her. But Rand defended herself, leaving a large scratch on her attacker's face, which helped the crew differentiate between the two Kirk "halves." After the situation was resolved, Rand continued as Kirk's yeoman until a reassignment in 2267. She returned to the Enterprise as transporter chief in the 2270s. (; )
Kirk and Rand repeatedly felt an attraction for one another, but resisted discussing or acting on their feelings openly. During one mission, Rand, Kirk and other members of a landing party were trapped on a planet where only children survived; adults quickly developed a deadly virus which had been accidentally created by a life prolongation project on the planet. When Rand became upset, Kirk held her close in his arms and comforted her. Miri, a teenage girl whom the team had befriended, witnessed this and became jealous. 
She felt that Rand was her "competition" and briefly betrayed the landing party by letting the other children abduct Rand. The captain's love for Rand became obvious when he was under stress from the disease, as he became distraught and obsessed in finding "his Janice," even grabbing Miri and shouting, "Where is she, Miri? Where is she, Miri? Where's Janice? Has something happened to her? Where is she? I've got to find Janice!"
Back aboard the Main Bridge, Kirk admitted, acknowledging that Miri's true age was far older than it appeared to be, "I never get involved with older women, Yeoman." Rand threw him an "Oh, really?" look in response. ()