Benjamin Sisko And Kasidy Yates-Sisko

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The relationship between Captain Sisko and Kasidy Yates was arguably Deep Space Nine's central love story. Sisko and Yates met in season 3 when they were set up by Sisko's son Jake. Although the romance went through some rough patches - with Kasidy even going to prison at one point - the love between the two endured, culminating in their marriage and Kasidy becoming pregnant in season 7.

In perhaps one of the saddest endings for any Star Trek relationship, however, the Deep Space Nine series finale saw Sisko sacrificing his own life and joining the Bajoran Prophets in their Celestial Temple. Sisko appeared to Kasidy in a vision, promising to return to her one day, although he did not specify when or how. The uncertainty surrounding when or whether he might be back at all put a tragic spin on Sisko and Kasidy's relationship, one that any Deep Space Nine fan is unlikely to forget as a heartbreaking part of the finale.

Worf And Jadzia Dax

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Worf joined the cast of Star Trek: Deep Space Nine in its 4th season, and he and the character of Lieutenant Commander Jadzia Dax had a connection from the start. Jadzia was very knowledgable about Klingon history and culture, something that made her and Worf become fast friends. The two realized that had developed feelings for each other in season 5, and began a relationship soon thereafter. They were married in the season 6 episode "You Are Cordially Invited".

Tragically, Jadzia was killed when she was attacked by Gul Dukat while visiting Deep Space Nine's Bajoran temple. Since Jadzia was a joined Trill, Doctor Bashir was able to save her symbiont, but he could do nothing about her injuries. Jadzia died with a heartbroken Worf by her side. Worf and Jadzia had been planning to have children, a fact which made her sudden death even more painful. The Dax symbiont was subsequently joined with Ezri Teegan, who became Ezri Dax. Despite developing a friendship with Ezri, Worf did not pursue a romance with his late wife's successor.

Neelix And Kes

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From their introduction, Neelix and Kes were very much the odd couple on Star Trek: Voyager. Although it was clear that they loved each other, Neelix sometimes struggled with jealousy and often treated Kes in a more paternalistic way than what she deserved as his romantic partner. The pair were introduced in Voyager's pilot episode "Caretaker" and were in a relationship throughout much of the first 3 seasons, although they broke off their relationship midway through season 3 after Kes was possessed by an evil alien warlord.

During her time on Voyager, Kes had been expanding her latent telepathic abilities. At the beginning of season 4, a sudden increase in her abilities caused her to transcend to another plane of existence, leaving Voyager and Neelix behind. By that time, Kes and Neelix were merely good friends, but her leaving ended any possibility of their relationship being rekindled in the future.

Chakotay And Seven Of Nine

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The romantic relationship between Chakotay and Seven of Nine evolved rather quickly during the second half of Star Trek: Voyager's final season. When Seven began further exploring the idea of dating on the holodeck, she developed romantic feelings for a hologram of Chakotay she had created. From there, the relationship began to evolve in real life, and by "Endgame", Seven and Chakotay had been on several dates. The two even expressed a more serious commitment to each other, despite Seven's fears about the future brought on by the knowledge of her death in an alternate timeline.

Up until recently, fans would have presumed that Seven and Chakotay's relationship continued after Voyager's return to the Alpha Quadrant. However, when Seven joined the cast of Star Trek: Picard in 2020, the show revealed that since Voyager's return she had left the Federation and joined a vigilante group in the Beta Quadrant. This in itself would not have been enough evidence of the end of her relationship with Chakotay, but the season 1 finale of Picard also showed evidence that Seven and Raffi Musiker were considering a romantic relationship with each other, a decision which added a completely new dimension to Seven's sexuality and effectively put any chance that she might still be with Chakotay to bed.

Trip Tucker And T'Pol

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Trip Tucker and T'Pol's romance on Star Trek: Enterprise was fraught with complications from the start. The two started as colleagues and reluctant friends, but after T'Pol aided Trip with his PTSD and grief over the death of his sister, Trip began to develop romantic feelings for her. Their relationship was extremely one-sided for most of its course, and at one point Trip even attempted to transfer away from Enterprise because of his feelings for T'Pol, but T'Pol convinced him to stay by stating that she reciprocated his feelings.

When their DNA was used to make a child, it seemed as though Trip and T'Pol would cement their romance by becoming parents, but genetic issues caused the baby's death, leaving the two of them heartbroken. After their daughter's death, the two broke things off for good, and any possibility of things resuming was cut short by Trip's death in the Star Trek: Enterprise series finale, "These Are the Voyages..."