In April of that year, following a disastrous engine test, the Pioneer became stuck in a decaying orbit of a super-Jovian planet. The crew was evacuated to the warp nacelle catwalks due to the planet's radiation ring. Kirk calmed down some of the enraged crew of the Pioneer, who blamed Tobin Dax's engineering team for the situation they were in. During this incident, he fell in love with Lieutenant Valeria Williams, the ship's tactical officer and security chief. Williams was initially not attracted to him and struggled to remember whether his first name was Sam or Stan. (ENT - Rise of the Federation novel: A Choice of Futures)
In 2164, the Pioneer was tasked with learning new information about the Rigel system before their admission into the Federation. During their cultural exchange, Kirk and the ship's communications officer, Ensign Bodor chim Grev, were invited to examine the archive on Rigel V. This turned out to be a trap as their guide, Rehlen Vons, turned on them with a group of Rigelians, killed their escort, Crewman Kenji Mishima, abducted the two officers and took secret data files from the archive.
Vons coerced Grev to decode the files by torturing Kirk. After a week, Grev was forced to show some results but tried to give them low level information. Their captor turned out to be a Malurian impersonating Vons, but was killed by his "allies". This made things even worse for the duo, and they begun considering to provoke their captors into killing them to keep the information from falling into the wrong hands. Fortunately they were rescued by Pioneer without any permanent injuries. After the incident Kirk decided to ask out Williams, but before he could she told Kirk that she saved an alien woman seriously delaying Pioneer's search efforts. Kirk took offense that Williams choice made his torture possible. (ENT - Rise of the Federation novel: Tower of Babel)
The two avoided each other for months. In May 2165, during the Ware mission, Kirk recorded the history of Kyraw, and how their homeworld fell victim to the Ware. (ENT - Rise of the Federation novel: Uncertain Logic)
Kirk and Williams later reconciled and began dating. Reed and Mayweather permitted this as it did not interfere with their work and they were in different departments. When Admiral Archer told Captain Reed that he had become aware through Captain Williams that the two were dating, Reed asked Archer to convey to Captain Williams that Kirk was an officer and a gentleman.
By 2190 Kirk had written The Forgotten Enterprise. In his work he stated that people had no control over whether or not they would be remembered as heroes or villains, and that the boldest could be remembered as both. (ENT - Rise of the Federation novel: Live by the Code)
On his website, Christopher L. Bennett, author of the Rise of the Federation series, noted that Sam and his romantic interest Valeria Williams were meant to be James Kirk's ancestors.
- Yes, Val and Sam are meant to be Jim Kirk’s ancestors—implicitly the parents of Tiberius Kirk and the grandparents of George Samuel Kirk, Sr. (as established in the 2009 film). This conflicts with a reference in the ST:TMP novelization to Samuel being the name of Kirk’s grandfather rather than his great-grandfather, but much from that novel has been superseded by canon. (And it’s confusing to have two Samuels herein, Kirk and Gardner, but that happens in real life sometimes.) Val is meant to represent Kirk’s tough, brash side, while Sam is his gentler, more intellectual side. The “Abraham” is in reference to Abraham Lincoln, Jim Kirk’s (and Gene Roddenberry’s) hero. 
Further, Kirk could be bisexual. In Live by the Code, Kirk playfully notes he can't reciprocate his friend Grev's affection. Bennett notes:
- 'I didn’t originally intend for Grev to be gay. It’s just something that happened to show up in his interactions with Sam and that I decided to run with. As for Sam, I was originally going to have him say “I wish I could return his interest, but I’m just not interested in men.” But then I thought it would be more fun to have him say “I’m just not attracted to Tellarites.” That leaves it more ambiguous, and makes it more about a future society’s priorities and preoccupations than our own.' 
|Federation Starfleet||Y. Achrati • Bergmann • Chen • P. Collier • T. Dax • C. Detzel • B. Grev • J. Guzman • Kano • Karthikeyan • E. Kemal • S. A. Kirk • Konicek • T. Liao • T. Mayweather • K. Mishima • P. Morrow • K. Ndiaye • A. Osunwoke • H. Polanski • M. Reed • R. Sangupta • A. Sheehan • R. Tallarico • A. Tatopolous • C. Tucker • V. Williams • S. Yuan|
- ENT - Rise of the Federation novel: A Choice of Futures
- ENT - Rise of the Federation novel: Tower of Babel
- ENT - Rise of the Federation novel: Uncertain Logic