Overall, I would describe this episode as exasperating. For one thing, it's exasperating to have Twilight going into crazy freakout mode yet again, complete with wacky distorted facial expressions, and to have this occur from the beginning of the episode. I just think that Twilight in crazy freakout mode is way too overplayed at this point; I just find it frustrating, and unbecoming of someone whom the show appears to be setting up as the soon-to-be leader of Equestria. However, another thing I find exasperating about the episode is how it focuses on Twilight as being essentially the only one in the wrong. Yes, it basically goes without saying that Twilight's rules-lawyering is obnoxious, that Twilight's purposefully tricking Pinkie into getting disqualified is underhanded, and that if Twilight is going to act this way, then she probably should learn not to do that. But I don't derive any pleasure or entertainment from seeing Twilight get her comeuppance in the last third of the episode; I just feel like Twilight shouldn't have been written to misbehave so badly in the first place. (And I sympathize with Twilight's frustration; if getting randomly paired with a bad partner for Trivia Trot is frustrating, try getting randomly and permanently paired with a bad partner or partners for a semester-long laboratory class, which happened to me multiple times.)
Moreover, I think that the lesson of this episode also implies that it was bad and/or wrong for Twilight to take Trivia Trot seriously, and to try to achieve three wins in a row. Instead, apparently, Twilight should have, and is made to, adopt Pinkie's attitude of "just having fun" and not taking the Trivia Trot game seriously. Meanwhile, there are evidently no lessons to be learned from anything Pinkie does, and no attempt is made to point out anything that Pinkie could have done better; she's essentially a pure victim, to whom Twilight is made to conform in the end. But I think Pinkie could have observed that many other players are taking this game more seriously than she is - particularly Twilight, who told Pinkie that winning this game is very important to her. And after Pinkie sees that this game is being played differently than she might have expected, then I think Pinkie could have either tried harder to do what Twilight asked her to do in order to win, or, if that turned out to be impossible, concluded that this game isn't for her, and voluntarily stopped playing. Finally, there's also a significant amount of weirdness concerning the rules of Trivia Trot and how the game was conducted, which contributes to the conflict and isn't really addressed in the episode.
First, I'll try to talk about the rules of Trivia Trot and how the game was conducted, and how those probably contributed to the whole conflict of the episode. To start off, we see that there's a literal book's worth of rules to the game, and those rules are laid out in a formal and complex way. So I would think, with the rules being as involved as they are, that it would be prudent to have potential players, and particularly new players, give some acknowledgement that they've read, understand, and agree to abide by all of these rules. And yet many of the players, and sometimes even Granny Smith as host and referee, don't seem to know or particularly care about the rules, which serves to fuel Twilight's rules-lawyering later in the episode. Even Sunburst, who cites rules by chapter and verse later in the episode, seemed not to notice or care that his teammate Cranky was sleeping (and snoring) right next to him, which is a rules violation worthy of disqualification, and results in Sunburst's being sidelined from the game until Twilight teams up with him. Why are there all of these rules if many of the players don't seem to be familiar with them, or seem to particularly care about following them?
And, in what might be an even bigger problem with this complicated rulebook, Pinkie appears to just walk in off the street and put her name in as a player with no questions asked. Is she aware that there's a literal book's worth of rules to the game that she has to follow? On the one hand, I wonder why neither Granny Smith nor anyone else asked Pinkie to acknowledge that she's read, understands, and agrees to abide by the rules, before she entered as a player. But on the other hand, perhaps it's known that Trivia Trot has this rulebook, and it's incumbent on any new players to learn and abide by the rules. And I don't think it's unreasonable to expect people to have some idea of how Trivia Trot is played before they enter as players. Pinkie demonstrates in the episode that she doesn't even know that a team can have negative points, and doesn't even know that answers must be specific and exact. Those seem like pretty basic things to know before starting to play the game. So it seems to me like there's blame to go around to both Pinkie and the people who are running the Trivia Trot game for this issue of Pinkie's not knowing and abiding by the rules.
It also just seems like the way that the rules are set up and that the game is played is asking for trouble. Trivia Trot has: (1) a complicated book's worth of rules; (2) the ability for anyone off the street to join the game, without any apparent demonstration of understanding and agreeing to abide by the rules; (3) having randomly and permanently assigned partners for the whole night, regardless of seriousness or skill level, unless your partner is disqualified and you find another person to take that partner's place; and (4) at least several players who take the game quite seriously and are looking to achieve or maintain difficult records. I would be kind of surprised if something like the events of this episode hasn't happened before. Maybe Trivia Trot was enough of a niche thing that the regular (and serious) players didn't have novices throwing a wrench in the works who don't know the rules and aren't taking it seriously, at least until Pinkie showed up and changed all of that. And just from observing this episode, is there really much to be gained from having randomly assigned partners, anyway? Trivia Trot appears to consist only of questions in which all teams try to answer as soon as possible; that format doesn't seem conducive to consulting with partners to come up with answers, particularly when those partners could be strangers who don't know anything about each other's knowledge bases or strengths and weaknesses.
Finally, there are at least a couple of other rules that seem strangely not well-thought-out. Why is sleeping during the game cause for disqualification and removal, but getting outside help to answer a question only results in the loss of a point? And if this game is going with having randomly and permanently assigned partners, then it seems like a significant oversight to allow, say, two players teamed with partners they don't want to trick or goad their partners into disqualifying themselves, and then allowing those two players to team up with no penalty. Does that make for a fun, fair, and entertaining game if players with partners they don't want end up more concerned with finding ways to dump their partners - or quitting - than playing the game? So I think that these Trivia Trot rules, and the way in which the game was conducted, are a significant contributing factor to the conflict of the episode.
Now I'll talk a little more about Pinkie's and Twilight's behavior in this episode. To start off, just after it's announced that Pinkie and Twilight will be partners (and after Pinkie does her "name the shipping names of Twilight x Pinkie" shtick), Twilight directly tells Pinkie that this is a special game for Twilight, that she's trying to get her third win in a row, which no one has done before, and that she's really hoping to do so. And Pinkie replies "You don't have anything to worry about. I'll do everything I can to be the bestest and most funnest teammate ever". Since it's established that winning this game is very important to Twilight, I might think that being the "best and most fun teammate ever" would mean letting Twilight - the veteran player who probably knows what needs to be done to win - to take the lead, and for Pinkie to try hard to do what Twilight wants her to do.
But then we get Pinkie not knowing the rules, and ringing in with overeager, long-winded and/or vague answers that result in a point loss. (I might also add that those things are a nuisance to everyone, not just Pinkie's teammate.) We also see that Pinkie can't even concentrate on the topic of apples for more than 2 seconds, and is distracted from ringing in by a normal body function. So what are we supposed to take away from that? Is Pinkie just not even trying to concentrate? Is she actually incapable of concentrating on a topic for more than 2 seconds? And in either case, why shouldn't we consider that Pinkie might just not be equipped or suited to play this game? In fact, I can't help noticing that four of the Mane Six are here playing Trivia Trot, and appear to be regular players, and yet this episode is Pinkie's first time playing. Had these four invited Pinkie to play before, but Pinkie was just always busy or declined for other reasons, and all of a sudden, in this episode, she decided to take them up on the offer? Or did the four of them choose not to invite Pinkie to Trivia Trot for a good reason - namely, that they think Trivia Trot (as it's being played) is ill-suited to what Pinkie normally likes to do?
And so, after trying to deal with Pinkie's behavior, I'm not surprised that Twilight resorted to tricking Pinkie into disqualifying herself. What should Twilight have done, if tricking Pinkie into being disqualified was underhanded? I don't know. I find it hard to believe that talking to Pinkie or continuing to try to coach her would have worked. By that point, I think that Pinkie had demonstrated that she couldn't be relied on to concentrate, ring in at the right time, and actually give correct answers, even if she might know them. And she also probably couldn't be relied on to contain herself, not be distracting, and generally refrain from ringing in, either. Maybe, if Cranky is sleeping during the game, and Pinkie doesn't have the requisite mindset (or knowledge of the rules) to play the game without being a nuisance, both of them could be asked not to play any more, and then perhaps Twilight and Sunburst could be made into a team, or something.
But the solution that this episode seems to come up with is that Twilight should just give up on her hope and dream of achieving 3 wins in a row, stop taking the game seriously, and conform herself to the way that Pinkie wants to play the game. And that's reinforced by Spike's telling Twilight that this is "just a game", and even by the pun in the title of the episode, which implies that the record which Twilight is pursuing is trivial. But I don't think that it's inherently bad or wrong to take a game (or other activity) seriously. In many cases, the fun and enjoyment of a game (or other activity) can come from taking it seriously, playing hard to try to win, and even striving to achieve and maintain records. So I don't like the implied message of this episode's resolution. Perhaps a point could be made that it's a fool's errand for Twilight (or anyone else) to strive to achieve or maintain records in a game where her teammate is randomly assigned, and could be a total novice who doesn't take the game as seriously as she does. But I would argue that there are potential solutions other than deciding that nobody should take Trivia Trot seriously. I could imagine, for example, having separate competitive and casual games of Trivia Trot, with the competitive games perhaps having stricter rules or standards about who can play or how teams are chosen, while people like Pinkie could just choose to play casual games.
Now here are the rest of my miscellaneous observations:
I didn't realize at first that Trivia Trot is being held in the Hay Burger as seen in "Twilight Time". Does the restaurant get any particular benefit from hosting Trivia Trot, or are they doing it just to be nice?
In the ongoing saga of trying to figure out when and why characters draw their cutie marks to represent themselves, as opposed to just writing their names, we see that Twilight and Pinkie drew their cutie marks to put in the bowl, but at least some other players did opt to write their names. However, we don't know who chose to write their names, or why.
When Rainbow tells Sunburst "I hope you realize not every category is gonna be 'Spells So Old, Not Even Star Swirl the Bearded Remembers Them', it took me a little bit to realize that that's not just a figure of speech; Star Swirl the Bearded is living right now in-universe and could actually be consulted about which spells he does or doesn't remember.
When Spike begins to roll up Twilight's scroll outside, he's rolling it with the writing facing inward, but when Spike opens the door and brings the scroll in, the writing is facing outward.
After Spike comes back in from outside with the rolled-up scroll, Twilight looks at it and we see a chart with 11 potential players down the side of it, including Mudbriar, Sunburst, and Pinkie. But how did they, and particularly Pinkie, get on the scroll? Twilight's bar graphs of potential teammates shown previously only had 7 people - Fluttershy, Applejack, Dr. Whooves, Rainbow, Bulk Biceps, Matilda, and Maud - and Twilight explicitly says that she hadn't anticipated Pinkie as a potential player. And we never see Twilight or Spike write on the scroll at any time between Pinkie's entering herself as a player and our seeing the scroll with 11 potential players on it. There is a jump cut between Spike's being teleported outside and when he walks back in, so perhaps he could have written on the scroll then, but Twilight only asked him to "find the part on matchups", not to write up new matchups including Pinkie (and the others).
Would an air horn of the size that Pinkie uses really be capable of making that loud or low-pitched of a blast?
Why did Applejack and Sunburst say that the scorekeeping job is intense, and try to dissuade Spike from doing it? As far as we see, he's not tasked with looking for rules violations or making judgement calls; essentially all he does is flip the digits representing each team's score.
Cranky actually goes from looking to be perfectly fine and awake to being fast asleep in about 3 seconds.
There are times throughout the episode when two characters just talk to each other for 10 seconds or more, even in the middle of the game, and all the while, seemingly nobody else is doing or saying anything. Does everyone else just wait silently and patiently for the two characters in focus of the camera to finish talking?
Some of the Trivia Trot questions seem quite vague, and I wonder if there would be more than one potential correct answer. For example, is there really only one place in the world that "used to be a cavern, but after thousands of years of erosion, is now a gorge"? Are Lord Tirek and Scorpan really the only ones in all of Equestrian history who "traveled to Equestria from a distant land seeking to steal the magic from its pony inhabitants"?
Throughout the episode, we only ever see teams earning 1 point for a correct answer, and sometimes losing a point for wrong answers or rules violations. Yet by the end of the episode, the 5 remaining teams have scores in the 40s and 50s. That seems to imply that at least 250 questions or so have been asked, and the game is still going on, with Twilight not even totally ruling out the possibility that she and Pinkie could still win starting from zero. So how long do these Trivia Trot games go? How many questions are asked by the end of a typical game? And since an intermission occurred earlier when the teams had 3-11 points each, how many more intermissions occur in a typical game?