DS9’s Captain Sisko was a widower, a father, and a war hero, but he also found time for love, and built one of Star Trek’s most enduring romances.

Star Trek: Deep Space Nine‘s Captain Benjamin Sisko (Avery Brooks) had fewer love interests than his predecessors, which was reflective of his solid and dependable nature. When Star Trek: Deep Space Nine began, Sisko was a grieving widower and a single father who didn’t have much time for romance. Unlike his predecessors, Captain James T. Kirk (William Shatner) or even Captain Jean-Luc Picard (Patrick Stewart), Sisko wasn’t spending every other episode romancing guest characters. It was just one of many innovations that clearly differentiated Star Trek: Deep Space Nine‘s characters from their franchise stablemates.

During production on Star Trek: Deep Space Nine season 2, producers Ira Steven Behr and Michael Piller were keen to define Sisko’s character, as he had become too detached. These discussions led to Sisko’s first romance in the episode “Second Sight”, and also helped to define Avery Brooks’ unique Star Trek character for years to come. Ira Steven Behr later reflected in the Star Trek: Deep Space Nine Companion that Sisko was envisioned as the “builder, he stays with a project until the finish.” Sisko’s approach to romance in Star Trek: Deep Space Nine perfectly reflected this characterization.

Benjamin Sisko was a father, a widower, a religious icon, a war hero, and a Starfleet officer, and his best DS9 episodes reflect his multiple facets.

5 Jennifer Sisko (Felecia M. Bell)

Star Trek: DS9, Season 1, Episode 1, “Emissary”

Star Trek: Deep Space Nine‘s pilot episode “Emissary” opens with the tragic death of Jennifer Sisko (Felecia M. Bell) during the Battle of Wolf 359. Later in the episode, after his first encounter with the Bajoran Prophets, Sisko relives the day that he first met Jennifer. Benjamin and Jennifer met on Gilgo Beach in 2354, where there was an instant attraction between the pair. They married quickly and their son, Jake Sisko (Cirroc Lofton) was born a year later, in 2355. Jennifer and Benjamin Sisko were together for 13 years, until she was killed aboard the USS Saratoga at the Battle of Wolf 359.

Jennifer’s death and the destruction of the USS Saratoga forced Ben to rethink his career in Starfleet until he was assigned to Deep Space Nine. Originally seeing DS9 as a temporary position, Sisko’s experience with the Bajoran Prophets allowed him to process his grief and trauma over the death of his wife, Jennifer. By the end of Star Trek: Deep Space Nine‘s pilot episode, Sisko has a renewed sense of purpose, and even appears to have moved past his disdain for Captain Jean-Luc Picard and his role in the Wolf 359 massacre. However, it’s also clear that Sisko’s still not ready to move on from Jennifer.

4 Fenna (Salli Elise Richardson)

Star Trek: DS9, Season 2, Episode 9, “Second Sight”

Fenna (Salli Elise Richardson) was the first woman that Sisko became romantically involved with in Star Trek: Deep Space Nine. Sisko and Fenna met late one night on the Promenade, and were immediately attracted to each other. Sisko’s demeanor changed overnight, as the new relationship had a positive impact on him, four years after Jennifer’s death. However, Fenna kept disappearing, which made Sisko suspicious, especially when he met her doppelgänger, Nidell. Tragically, Sisko’s romance with Fenna couldn’t last because she was merely a projection of the unhappy Nidell’s unconscious mind. After Nidell suppressed Fenna, neither she nor Sisko seemed interested in pursuing a relationship with each other.

3 Mirror Jadzia Dax (Terry Farrell)

Star Trek: DS9, Season 3, Episode 19, “Through the Looking Glass”

Commander Benjamin Sisko had a one-night stand with the Mirror Universe counterpart of Lt. Jadzia Dax (Terry Farrell) in Star Trek: Deep Space Nine season 3. In the episode “Through the Looking Glass”, Sisko is taken to the Mirror Universe to stand in for his own Terran counterpart, whom it’s discovered was having an affair with the Mirror Universe’s Jadzia Dax. A Dax and Sisko love story felt like a fascinating avenue for DS9 to explore in the main timeline, but they instead settled for this wryly humorous scene in which a put-upon Sisko has to sleep with Mirror Jadzia, so he doesn’t raise suspicions about his true identity.

The Mirror Universe is home to the darkest and most depraved versions of our favorite Star Trek characters, but which of these variants is best?

2 Mirror Jennifer Sisko (Felecia M. Bell)

Star Trek: DS9, Season 3, Episode 19, “Through the Looking Glass” and Season 4, Episode 20, “Shattered Mirror”

Later in “Through the Looking Glass”, Commander Sisko has to carry out his mission for the Terran Resistance; recruit Jennifer Sisko. In the Mirror Universe, Benjamin and Jennifer had a far more tumultuous relationship, and had become estranged. Smiley O’Brien (Colm Meaney) hoped that Prime Sisko could convince Jennifer to join the Terran Rebellion, which provided some complicated feelings for Benjamin. Although Sisko resists temptation, there are some occasionally tender moments between him and his wife’s Mirror Universe counterpart. It’s the dependable and loving side of Prime Sisko that eventually convinces Jennifer to join the resistance.

Mirror Jennifer Sisko returned in Star Trek: Deep Space Nine season 4, episode 20, “Shattered Mirror”. This complicated matters further, as Jennifer formed a bond with Jake, whom she had kidnapped to convince Sisko to build the ISS Defiant. Jake and Jennifer even began forming a semblance of a mother and son relationship, much to Sisko’s concern. Tragically, Mirror Jennifer was killed during Sisko and Jake’s escape back to the prime Star Trek timeline, forcing father and son to grieve their loss all over again.

1 Kasidy Yates (Penny Johnson Jerald)

Star Trek: DS9, Season 3, Episode 23, “Family Business” onwards.

Jake Sisko introduced his father to Kasidy Yates (Penny Johnson Jerald) in Star Trek: Deep Space Nine season 3, episode 23, “Family Business”. Ben and Kasidy bonded over a shared love of baseball, and they quickly began dating. Kasidy was a freighter captain, and so they often spent long stretches of time apart. However, the biggest challenge for Kasidy and Sisko’s relationship in DS9 was when she was convicted of smuggling supplies for the Maquis. However, Ben and Kasidy weathered that particular storm and emerged stronger than ever.

Benjamin Sisko and Kasidy Yates married at the height of Star Trek: Deep Space Nine‘s Dominion War, despite the warnings of the Bajoran Prophets. Tragically, Captain Sisko was summoned to the Celestial Temple by the Prophets after defeating Gul Dukat (Marc Alaimo) in the Bajoran Fire Caves. Benjamin promised to come back for Kasidy, Jake, and his unborn child, but the fate of Star Trek: Deep Space Nine‘s Captain Sisko has never been confirmed on screen. However, Kasidy and Sisko endured imprisonment and galactic war, so the Bajoran Prophets don’t stand a chance against the power of their love for each other.