"Elaan of Troyius" was written and directed by John Meredyth Lucas
Ah, the old "arranged marriage for peace" story. With a few twists. I'm pretty sure, even as a kid, I got the "Helen of Troy" joke. (For those who don't, Helen was said to be the most beautiful woman in the world. She was given as a trophy to the Trojan, Paris, for choosing Aphrodite as the Fairest in a contest of Goddesses. Helen was already married and her husband raised an army of Greeks to get her back, leading to the decade-long Trojan War.) However, I don't think I was old enough to realize this steals quite a bit from The Taming of the Shrew.
The influences and retellings are interesting for sure.
What stood out to me the most, though, was the acting - France Nuyen and Jay Robinson easily steal the show with superb acting of the material.
The Enterprise picks up Elaan, the Dohlman of Elas, to take her to Troyius, where she is to be married to their king in order to stop the two peoples from killing each other. Ambassador Petri of Troyius is along to teach her Troyius' culture. She is haughty and imperious and it's obvious she really doesn't want this. She has 3 guards with her, the lead of which is Kryton. The Enterprise travels at slow impulse to give the Ambassador time to do his job.
In ways, there's casual sexism, but I also sat in the last rewatch and fathomed if Elaan was a dude. I don't think it's always sexism as it is just a level of decorum or the idea of a leader acting like a preschooler, even if the story is rough around the edges, also trying to be comedy that - even in 1968 - may not have landed.
Also being a discussion on speciesism/racism, Kirk's got a great line about prejudice. If not ironic at times as Kirk, despite being ordered to be a taxi service, didn't read up on the Elaasians at all.
A Klingon ship is following, but doesn't appear to want to attack. No one knows why they would want this system.
It's a terrific mystery, hidden in plain sight as the dilithium reveal is later in the story. The use of "top secret mission" at the start ensures the crew are just as much unaware as the audience, and who would have guessed that the stones deemed most precious in one scene was deflection from another necklace, whose "commonplace" stones were of the very dilithium at the crux of all this. That subplot definitely is a positive.
Petri is having a hard time dealing with Elaan. After Kirk gives him bad advice, Elaan stabs Petri, who survives but wants nothing to do with the Dohlman now. Kirk takes over as her teacher. She throws a "why does nobody like me" fit and cries, which Kirk wipes away. Elasian women's tears have a biochemical that acts like a super love potion on men. Kirk falls for her quickly.
The Dohlman not realizing the need, I'm a little amazed that there was this much going on for a diplomatic mission.
Meanwhile, Kryton sabotages the warp engines and contacts the Klingon ship. When captured, he kills himself. Elaan says that he was in love with her and against the marriage. It turns out Kryton rigged the ship to blow up if it went to warp. The dilithium crystals are burnt out and so the Enterprise has no warp and no weapons as the Klingons attack. Elaan appears on the bridge, but Kirk sends her to Sickbay as it's the safest area of the ship.
The plot thickens. It's nice that Kryton was doing this not as much to help the Klingons by direct help (would he care about any visitor from another star system unless they offered some assistance, so he too was likely being used), but because he wanted the Dohlman and loathed the idea of her and some other guy in an arranged marriage. I wonder if Kryton had been inflicted with the teardrop secretion as well. I wonder what the Troyian leader was expecting or why we see nothing of their system, apart from the ambassador. Would he be nonplussed or would he be upset over this arrangement as well.
It did bug me that Scotty said that the whole assembly was burnt out and irreparable, then immediately in the next scene it's all of a sudden "We need crystals and then it'll work". A slight rewrite would have fixed that, but it's a small thing. Especially considering how well the construction of the subplot hiding the dilithium as being a big factor was handled.
In Sickbay, Ambassador Petri begs Elaan to accept a necklace of Troyian royal jewels. Elaan accepts and goes back to the bridge. Spock detects strange energy readings from some of the jewels; Elaan describes them as common stones. The stones are actually dilithium crystals, which explains the Klingons interest in this star system. Scotty and Spock jury-rig the necklace into the warp drive. Enterprise manages to shoot photon torpedoes at the Klingon ship, damaging it and driving it away.
A great reveal and largely great action scene. The nitpick is using warp drive a little too much, given how fast warp speed is. Trying to scare Kirk into jumping to warp was a brilliant start. Even more brilliant if Kirk made the order and the Enterprise exploded, thus requiring a pair of sunglasses, sunblock, and a nice glass of Piña Colada to down in the process.
Elaan leaves for Troyius, giving Kirk a dagger as a memento. McCoy finds an antidote to the tears, but "The Enterprise infected the Captain long before the Dohlman did."
That ending where Kirk's adrenaline is so sappily glossed over. Oh, he loves the ship more. Being humanoid still means some substances won't always have the same effect. Unless that was the intent, to not use that exposition because "Kirk is so much male that his adrenal glands produce the cure for everything. yes, everything." Ugh.
Elaan may be a spoiled brat, but I totally understand her not wanting to be used as "a bribe to stop a war." I'm undecided if she cried on purpose to manipulate Kirk or if she was just crying from frustration and infected him. She seems genuinely sad to leave him in the end.
+1 There is far more complexity to Elaan than what's hinted at, and we get nothing on the Troyians except an assumption.
I love how it's left ambiguous as, in both cases, there's a reasonable explanation.
I think she was smitten by Kirk's brilliance; it falls in line with the episode's catering to the leader-types (who are important!) but denigrating everyone else in the process (Scotty too has a rather needed purpose as the lead expert in Engineering.)
60s Sexism: "Mister Spock, the women on your planet are logical. That's the only planet in this galaxy that can make that claim."
That one is utter cringe. It's there
possibly to appease the censors of the time, but even then, I doubt it. But it made Kirk's line about prejudices stand out more in the other scene. I wonder which line came first when the script was developed. Well, Kirk's line about prejudice is said first in the story, but in the scriptwriting process did that line lead to that line to Spock by intent.
I liked that Uhura gave up her quarters for Elaan. The set dresser did a nice job of having various African objects around the room.
Ditto. I noticed the details as well. As little as Uhura gets in dialogue this episode, what little she does say, and her quarters' backdrop, still get to say a lot about her and that's a big plus.
Shatner does a nice job this episode, especially when he's being vulnerable with Elaan and when he's struggling to not be distracted by her. France Nuyen does a great job playing our "shrew". Character actor Jay Robinson is excellent as Petri.
Ditto. The acting is excellent all around, uplifting what could have been a shambles.
Costuming: I like the initial purple outfit. I wonder if Perez was inspired by it when drawing Starfire's original costume in the comics. The silver outfit does nothing for her. The marigold dress is quite nice, but the blue wedding dress (completely open on the sides) is a stunner.
Definitely nice! TOS always had great costuming, especially for the newness of color TV. Whoever was at the wheel, the color wheel, knew their color theory eminently well in this show. It's a uniquely 60s thing, but it's great how much time they took to balance every conceivable palette and not sticking to just a simple one (e.g. teal/orange/red). Also, William Ware Theiss never ceases to amaze, and considering season 3's budget cuts, finding cheap plastic placemats repurposes for the security guards (who also get to show off their legs) are fairly convincing. They also predate the late-80s shoulder pad fad, but I'm not complaining, which is sad as I love to complain...
It's a B or B+ for me. Not the best of TOS or of season 3, but remove the obvious sexist bit and then thinking through what isn't due to sexism but general behavior, as well as the terrific handling of the diplomatic mystery, and it's almost underrated.
).
) high up on the inside" to help the Federation spies (Kirk and Spock); I vote for Sub-commander Tal. 
