WARNING: This article contains SPOILERS for Star Trek: Strange New Worlds season 2.Famously, Star Trek's Captain James T. Kirk (William Shatner) never married, but he had no shortage of love interests in both his personal and professional lives. Many of Kirk's most important relationships were from before he assumed command of the USS Enterprise, but two particular ex-girlfriends would return to play a big part in his later life. During his five-year mission on the Enterprise, Kirk had no time for serious romantic relationships, with one or two notable exceptions. However, he certainly gained a reputation as a ladies' man during Star Trek: The Original Series.
That reputation also defined Chris Pine's interpretation of Kirk in the J.J. Abrams movies. One of the earliest scenes in Star Trek (2009) saw Kirk attempt to hide from Cadet Nyoyta Uhura (Zoe Saldana) after a one-night stand with her Orion roommate. Star Trek: Strange New Worlds' James T. Kirk (Paul Wesley) doesn't appear to be the same lothario, although viewers have only been introduced to two alternate reality versions of Captain Kirk thus far. One of these Kirks has left a lasting impression on Lt. La'an Noonien-Singh (Christina Chong), but on the basis of the Enterprise Captain's extensive romantic history, a romance between La'an and the Prime Universe Kirk may already be doomed before it starts.
13 Ruth (Star Trek: TOS, "Shore Leave")
In the Star Trek: TOS episode "Shore Leave", Kirk and the crew took some much-needed rest on a planet in the Omicron Delta region. Typically, for Star Trek, the planet where everyone's dreams became a reality was too good to be true. When Kirk beamed down to the planet, he was greeted by Ruth, a lost lover from his days at Starfleet Academy. This was a robot duplicate of Kirk's former partner, but the original script revealed that Kirk and Ruth separated at some point during his first "star cruise". This choice between Kirk's love life and his life among the stars would become a recurring pattern.
12 Dr. Janice Lester (Star Trek: TOS, "Turnabout Intruder")
Sandra Smith is the only actress who played Captain Kirk when her character Dr. Janice Lester swapped bodies with the Enterprise Captain. Prior to Janice's elaborate power grab, she was in a year-long relationship with Kirk while they both studied at Starfleet Academy. Janice was unable to progress within Starfleet and felt that this was because of sexism. Kirk's own progression led to her resentment toward him, resulting in the relationship breaking down. Years later, she lured Kirk into an elaborate trap to steal his body and finally become Captain of the Starfleet flagship.
11 Dr. Carol Marcus (Star Trek II: The Wrath of Khan)
Prior to assuming command of the USS Enterprise, the young James T. Kirk was in a relationship with Doctor Carol Marcus (Bibi Besch). It's been teased that Kirk and Carol will be together during Star Trek: Strange New Worlds season 2, providing a chance to learn more about the young couple and their eventual breakup. Kirk and Carol's careers were incompatible with a lasting and committed relationship because he was a Starfleet officer, and she was a dedicated scientist.
It's possible that Marcus is the "blonde lab technician" introduced to Kirk by his old friend Gary Mitchell as it was revealed that Kirk almost married this technician. Kirk and Carol were similarly serious, as they had a child together - David Marcus (Merritt Butrick). Kirk agreed not to be part of David's life, something he would later regret when he was reunited with Carol in Star Trek II: The Wrath of Khan. Tragically, David was killed on the Genesis planet, and the grief of that loss was seemingly too great to ever reunite Kirk and Carol romantically.
10 Doctor Janet Wallace (Star Trek: TOS, The Deadly Years)
In "The Deadly Years", Kirk was reunited with another female scientist with whom he'd had a short-lived romantic relationship. Again, differences related to their careers drove a wedge between Kirk and Janet, leading to their breakup. Now a married woman living on Aldebaran III, Dr. Janet Wallace (Sarah Marshall) was instrumental in curing Kirk and the crew of the Enterprise of a deadly virus that caused rapid aging. To make matters worse, the Enterprise was also attempting to outrun the Romulans when the crew was stricken by the sickness, so it was thanks to Janet that the Enterprise survived the encounter.
9 Lt. Areel Shaw (Star Trek: TOS, "Court Martial")
During Kirk's Star Trek: TOS court-martial, the prosecuting attorney was Lieutenant Areel Shaw (Joan Marshall), who was another ex-lover of the Enterprise Captain. Thankfully for Kirk, Areel was never less than professional during his trial. The fact that Kirk and Shaw parted their relationship as friends was presumably a contributing factor to her impartiality during the trial. Kirk had committed no offense and was being framed by a former friend Lt. Benjamin Finney (Richard Webb). Realizing this Areel accepted that the charges should therefore be dropped, and she left the Enterprise, kissing Kirk goodbye.
8 Lenore Karidian (Star Trek: TOS, "The Conscience Of The King")
Kirk fell in love with Lenore Karidian (Barbara Anderson) the troubled daughter of Shakespearean actor Anton Karidian, alias of the brutal executioner Kodos (Arnold Moss). Refusing to believe that her father could be such a monster, Lenore murdered those who could connect Anton to his brutal past. Kirk's relationship with a serial killing actress could not last, and he had the young woman institutionalized for her crimes. However, his refusal to it his feelings for Lenore to Dr. Leonard McCoy (DeForest Kelley) suggests that Kirk had formed a deeper bond with the actress than it first appeared.
7 Edith Keeler (Star Trek: TOS, "City On The Edge Of Forever")
Star Trek: Strange New Worlds recently remade one of the greatest Star Trek: TOS episodes, "City on the Edge of Forever", by having La'an fall in love with a man who had to die to save the future. Interestingly, that man was an alternate reality version of the Captain James T. Kirk who would have to make a similar decision many years later. In "City on the Edge of Forever", Kirk fell for the progressive Edith Keeler (Joan Collins), who in many ways embodied the very ideals that built the United Federation of Planets. Sadly, Edith was ahead of her time, and her teachings about peace, love, and understanding would have inadvertently allowed the Nazis to win World War 2. Aside from Carol Marcus, Edith Keeler is the most impactful Kirk relationship in the whole of TOS, because of the tragic decision he was forced to make.
6 Miramanmee (Star Trek: TOS, "The Paradise Syndrome")
As Kirk was suffering the effects of amnesia when he entered into a relationship with Miramanmee (Sabrina Schariff), it's arguable that she doesn't count on the list of his love interests. However, the relationship between "Kirok" and Miramanmee was another huge tragedy for the Enterprise Captain. An amnesiac Kirk was believed to be a god by a pre-warp society and fell in love and married MIramanmee, who became pregnant with his child. Horrifically, mother and child were killed by a primitive and brutal stoning when Kirk's godlike powers failed to prevent an asteroid from hitting the planet. The grieving Kirk stayed with his wife as she lost her fight for life.
5 Shahna (Star Trek: TOS, "The Gamesters Of Triskellion")
Kirk's relationship with Shahna (Angelique Pettyjohn) in "The Gamesters of Triskellion" is where the much-parodied "human thing we call...love" scene comes from. In the episode, the Providers pit humanoid species against each other in combat, kidnapping Kirk to participate in their games. Kirk is trained by Shahna, whose eyes he opens to the wider universe and the human concept of love and romance. When Kirk and his fellow crew are rescued by the Enterprise, Shahna asks to go with them. However, Kirk decides that she'd be better off learning a new way of life on Triskellion, instead. It's likely that Kirk never really loved Shahna and instead saw her as a means to escape the planet with his life.
4 Antonia (Star Trek Generations)
When Kirk and Picard met inside the Nexus in Star Trek Generations, Kirk had, technically, been in a 75-year-long relationship with the unseen Antonia. In his Nexus fantasy, Kirk and Antonia lived on the Idaho farm of Kirk's Uncle, with a dog and several horses. It was the idyllic retirement that Kirk couldn't allow himself when he met the real Antonia after he first left Starfleet in 2281. Kirk revealed to Captain Jean-Luc Picard (Patrick Stewart) that he regretted never having proposed to Antonia, but now the Nexus allowed him to live out that fantasy.