Is Mr. Poe really as dim-witted as he seems, or is he simply unsure of how to act in such bizarre, tragic circumstances, and his attempts to sympathize with the Baudelaires simply come off as condescending? Also, could he have a mental condition? Not being able to recognize Count Olaf, or, rather, not Count Olaf, point-blank is stretching disbelief. "Face blindness" is a real condition, though Poe doesn't exhibit it with anyone else. Although he doesn't recognize Sunny at first in "The Penultimate Peril," and even says that she reminds him of a toddler he knows but doesn't put together that it's actually her. It's a very real possibility that Mr. Poe only recognizes the Baudelaires because there are three of them together, and he definitely could have at least some form of prosopagnosia. He himself admits that he can't remember a name or face in the same episode.
After their marriage was performed, Olaf reaches out to Violet for a kiss, though he quickly abandons that effort when she winces and turns away. Was Olaf really attracted to Violet in that fashion, or was he just trying to Squick her out for fun? If he was (bleurgh), did he refrain from kissing her due to minimal standards of consent or knowing better than to assault her in front of an audience?
Does Uncle Monty really think Stephano is just a spy from the Herpetological Society? Since he had a message from VFD saying the children were not safe and he is aware of Stephano threatening the children with a knife and the possibility Stephano wanted to murder him, could he have just been playing Olaf?
Aunt Josephine finally stands up to Count Olaf, she gives him a "The Reason You Suck" Speech before correcting his grammar. Was all the previous talk just bluster and her real point of contention his grammar or it an Arson, Murder, and Jaywalking speech summarising his crimes and failures before moving on to his grammar?
On that note, Olaf mentions that he used to make shredded beef tamales for Josephine's husband Ike. As Ike ate beef tamales before his untimely death, did Olaf intend to kill Ike, or was it a genuine accident or even a separate instance? If so, was it out of revenge or, seeing that the Vile Village bar mentions Josephine as one of his past lovers, to Murder the Hypotenuse?
The theme song "Look Away," sung by Count Olaf's actor, Neil Patrick Harris. On the one hand, it might just be a standard case of Lemony Narrator in line with how Snicket begs the viewer not to read his story. On the other hand, seeing as it is Harris, he might be singing the song from Count Olaf's POV demanding the audience look away so as not to witness his crimes or simply mocking the audience for their curiosity and the Baudelaires for their tragedies.
Some people believe the Hook-Handed Man's protectiveness of Sunny comes from the fact that he has a little sister of his own from who he's grown estranged. Confirmed by the third season.
Count Olaf brags about having an IQ "in the upper double digits", which places him at below-average intelligence. Is he simply ignorant and mistakenly believes that his score is high, or is he familiar with the scale but views it as a good thing in line with his anti-intellectual views that distinguish him from the members of VFD?
In "The Penultimate Peril", was Justice Strauss begging the Baudelaires to stay with her just her being Too Dumb to Live, or did she already have a plan to save themselves? Seeing that she made it back down safely and the Baudelaires could have very well died in their parachuting escape attempt, were running away with the abusive and murderously insane Count Olaf and the children nearly ended up indoctrinated into a cult and dying, she does have a point.
In "The Hostile Hospital", did Olaf intend to force Klaus to kill his sister, or was he planning on intimidating him into surrendering and leaving with him?
In "The Carnivorous Carnival", did Violet and Klaus simply plan to push Olaf down when they lured him to the lion pit or in a darker light, a murder-suicide, with one of the siblings grabbing Olaf and dragging him down with them so Sunny and the other could escape?
Did Esmé and Carmelita bypass poisoning the court with the Medusoid Mycelium out of stupidity? Out of justified worry that the Medusoid Mycelium will affect everybody? Out of moral standards or legal worries over mass murder? Or just to screw over Olaf for breaking up with Esmé the previous night?
Olaf's behavior in "The End"; being particularly idiotic even for him could be a breakdown after everything that's happened (especially since towards the end he starts acting more intelligent again).
In the opening scene, Olaf speaks to the Baudelaires jollily and even calls them his "henchpeople". On his time stuck with them, could he have grown to see the Baudelaires as his henchpeople (at least a replacement for his troupe) and even as "friends" or allies?
Did Gregor Anwhistle have sinister intentions experimenting with the Medusoid Mycelium, such as creating a bioweapon, or did he have more benign reasons, such as creating a medicine?
