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When people think of Deanna Troi's love interests on Star Trek, it'd be difficult not to focus on her longterm on-again-off-again affair with none other than First Officer of the U.S.S. Enterprise, William T. Riker. Though full of its own ups and downs, this relationship eventually ended in marriage between the two, and when we last saw them in Picard, things seemed to be going pretty smoothly. This is one of the great romances of Trek fandom, but let's be honest, Riker didn't always treat Troi right, and her acceptance of his proposal in Star Trek: Insurrection definitely required more than a little bit of forgiveness on her part.
At the end of the day, despite her impossible position of being apparently the only counselor to a crew of what we assume to be hundreds of officers, Deanna Troi is a character who didn't always get the respect she deserved. One need look no further than her tumultuous romantic life to see that people projected a lot of their own baggage onto our beloved Betazoid. Still, rather than playing the lovelorn fool to Riker and company, she was putting herself out there and embracing new experiences all the while. If there's anything we love, it's a lady who steers her own fate... despite the parade of jerks that writers trotted out as love interests for her.
The TNG episode "Loud As A Whisper" introduced us to Riva, a diplomat in the middle of negotiations who is deaf and uses a chorus of three who are telepathically linked with him in order to communicate. This story makes a kind of great statement about disability when Riva sharply scolds Picard for speaking to his translator rather than directly to him. Riva is a pretty interesting character, and the idea of having a full three-person Greek chorus behind him, helping him share his thoughts and feelings with the world, is something that could have gone in a lot of cool directions if he had returned, or if said chorus didn't end up vaporized right down to their skeletons halfway through the episode. Which they do.
Was he a good match for Troi? Not really, but so few people are. Her role in this episode is mostly her graciously withstanding some aggressive flirting, so we don’t get a lot of insight into what her feelings for Riva were. Still, she does seem to genuinely like and understand him on some level, and she helps him a lot when he is traumatized by the aforementioned vaporizing. Though we're not totally sold on Riva, he's still better than...
The episode "The Price" examines the negotiation tactics between different species when the Barzan open up bids on a wormhole in the Federation's sector of space. At the table in this bidding war are the Chrysalians, the Caldonians, the Federation, and, sadly, the Ferengi. Though Picard tries to oust the Ferengi immediately, the Barzan are a bit more diplomatic and invite them to join in on the talks. Meanwhile, the Chrysalians have sent along Devinoni Ral as their hired negotiator, and he immediately goes all-out trying to woo our girl Troi.
This story is an interesting one for Troi because Ral uses his own empathetic powers to gain an edge in negotiations and to manipulate others. When she calls him out about it, he claims that she does the exact same thing. That is what we like to call a false equivalency, but Troi does take time to consider the morality of her powers. She struggles with her attraction to him but ultimately refuses to allow him to gaslight her. She discovers that he has teamed with the Ferengi in secret and she confronts him about it. There might have been a spark between them, but Troi chooses her morality over Ral without much ado. When he says that he doesn’t like the part of himself that Troi has shown him and asks her to come along to help him be a better man, Troi declines. Choosing between one’s own life and career or "helping" a man act like a human being might not have been as difficult a choice as this episode makes it out to be, but, as always, we remain Team Troi all the way.
"Haven" featured the first appearance of Troi’s mother, Lwaxana, so that's pretty much the most important thing in the episode. In fact, it’s kind of difficult to even remember what happens outside of that. We are Lwaxana stans all the way, but allow us to shift our attention ever so slightly to her long-suffering daughter Deanna. Lwaxana announces that the time has come for Troi to enter into an arranged marriage with Wyatt Miller, a doctor with whom she has little to no chemistry. Though the two of them are friends, they both struggle with the idea of entering into a life together. In fact, Wyatt manifests another wife and takes off with her pretty fast. These are two people that just flat out did not want to marry each other, and that's OK.
Wyatt and Deanna are a bafflingly bad match, and so this episode is mostly just the backdrop that had to exist for us to be blessed with the greatness of Lwaxana Troi. Still, there is some quality healing between Troi and Riker, and at least the arranged marriage is quickly forgotten. Bye, Wyatt! Never talk to us or our Betazoid daughter ever again!
"The Masterpiece Society" is about a group of humans that have started a civilization on a planet that was long suspected to be uninhabited. When the Enterprise reaches out to warn them of possible impending doom, they grudgingly respond, but they make it very clear that they want little contact with outsiders regardless of their intentions.
Aaron Conor is placed in the position of whether or not to allow people into this closed society in order to save it, and he wavers throughout the episode, as do most members of the Enterprise crew. He does take a short break from waffling to enjoy a brief romance with Troi. Though his world closed its borders, his heart could not. Troi feels a little off-kilter in this episode and has a weird level of loyalty to Conor, but she and he both ultimately choose their duty over their attraction to one another. A boring end for a boring love!
Sure, Deanna and Riker had the love of a lifetime, but what about Deanna and Thomas Riker? In the episode "Second Chances," Deanna comes face-to-face with a Riker who had been stranded years ago and found himself unable to communicate with the outside world. While our Riker had quickly escaped and continued on, this Riker was run aground and left for dead. When he sees Deanna, he rushes forward and kisses her, to which she awkwardly responds that a lot of things have changed between them over the years.
This episode is interesting because Riker is given a second chance with Troi and he still botches it exactly the same way he did the first time. Riker himself is there to warn her that the other Riker will likely make the same choice he himself did, but Troi goes ahead and proceeds with a short fling with Thomas. Though the series writers tended to focus on Troi as being the one who was the most heartbroken over the end of her relationship with Riker, this episode gave her more strength by showing the ways that she herself had chosen her own career over their relationship in much the same way Riker had chosen his. When Thomas does indeed urge Troi to put her career on hold so that he might pursue his, she declines, not because she doesn't care, but because she has worked to build her own life. Yes, Troi!
First off, Worf isn't exactly a strange love, because he made a lot more sense than… well, frankly, every other character on this list. Truth be told, many of us are fully sold on the Troi/Worf ship in ways we remain to be with Troi/Riker. Despite the fact that their whole relationship is generally referred to as an inexplicable quirk of the final season, these two complimented one another in some surprising ways. Troi always compelled Worf to examine his feelings, and even in his early, more aggressive days on the show, Worf took the time to listen to Troi, even if he didn't agree with her. The respect they showed each other as co-workers and friends was truly inspiring, but as lovers, things got even more interesting.
The fact is, it's not all that surprising that the sensitive and perceptive Troi was attracted to the stable and consistent Worf after a handful of non-starter relationships with a small parade of self-involved jerks (see above). For his part, very much in contrast with the others, Worf always took the time and struggled with his feelings inwardly before he made them known to the world, making him a loyal and dedicated partner for Troi. In the final episode of TNG, Riker asks Troi if she's free for dinner, and she declines because she's already made plans with Worf. Frankly, though we love Troi and Riker, we were pretty okay with that ending. To the fanfiction archives, Worf/Troi shippers! We shall see you there.