The Doctor makes a bet with Tom Paris: that he can teach Seven of Nine enough about socializing and etiquette for her to go on a date with a member of the crew. But along the way, The Doctor discovers he has feelings for Seven himself. Meanwhile, when an ambassador of a strictly religious species overindulges in pleasures during his visit to Voyager, the crew must find a way to sober him up and hide the transgressions from his superior.
Star Trek generally is all about contorting other genres into a science fiction mold, but "rom com" isn't a genre the franchise tried often. Combining that with a frat-like screwball subplot makes this one of the lighter episodes of Star Trek: Voyager. Assuming, at least, that you find the formula of My Fair Lady to be light or romantic more than chauvinist and creepy.
This episode offers plenty to fit both categories. The Doctor is kind of "gross" in a lot of scenes in this episode. He alters Seven's appearance, drives her to socialize at a pace she would not choose for herself, actually inserts himself into Seven's date as the bar's piano player... and of course there's the bet with Paris. Generally, his gleeful planning of lessons on dating is hard to watch; considering his own lack of experience in the matter, it really borders on mansplaining. And then he goes full Barclay in the end, simulating his own crewmates (well... one of them, at least) for a holodeck scenario.
But there are more genuine moments too. Seven refers to the easy rapport she has with the Doctor, and we see that in several scenes. The moments that the two sing together arguably go on for too long, but the two actors (and characters) are very good together, and there's the sense of actual story being told through the songs. And Jeri Ryan nails many more scenes throughout the episode, from the comedy of Seven's awkward date with crewman Chapman, to the suave sophistication of Seven's simple toast, to the defiant moment where she tells off Paris over making the bet.
There are good moments for many for the other characters too. B'Elanna's reaction to being scientifically observed by Seven is a lot of fun. Kim setting his own infatuation aside to help Seven pick someone for her date marks a nice bit of growth. And the way Paris is ultimately supportive of the Doctor telling Seven how he feels is actually touching.
I also find the subplot quite successful -- it's sort of one thread of the middling Next Generation episode "Liaisons" given more space. But they wisely cast Kids in the Hall veteran Scott Thompson as the alien ambassador, and then actually allow him to play the role broadly. He cavorts around drunkenly, raving until he passes out, and being genuinely funny.
Other observations:
- It has always seemed like you really can just walk in on anybody's holodeck scenario at any time, but here we actually see Tom Paris do it at one point. (Fair enough; they take his Sandrine's Bar program for their own use.)
- Besides Scott Thompson, there are two other recognizable guest stars. Brian McNamara, who plays Chapman, has done like one episode of every television show that aired in the 1990s. And Ian Abercrombie will be recognizable to anyone who watched Seinfeld (as Elaine's boss, Mr. Pitt).
I do love that this episode is very much "about the characters." And I like that the subplot is legitimately funny. But in an episode that really is just "Star Trek does My Fair Lady," for me to feel that the episode is "good except for the My Fair Lady parts" does mean I had problems with the entire thing. "Someone to Watch Over Me" is funny, sweet, and a good showcase for the performers... when it's not old-fashioned, creepy, and awkward. I'll average that all out to something like a B+.
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