In this comic, we find out that robots determine their gender based on how much talking they do. At first this sounds like something stereotypical and trite...until you realize that the robots only barely understand humanity. Stereotypes are pretty much all they have to go on.
Despite a highly honed sense of self-preservation, Sam enjoys doing things with a high degree of danger and risk. Then we learn that mating is fatal for his species, those of his species capable of breeding do so young, and no member of his species has died of old age. Sam's race effectively has no biological incentive for long-term self-preservation, leading them to take crazy risks in the name of being remembered as they get older.
One wonders how Sam could have accumulated so much debt, when you'd think everyone would know not to loan him money...until you realize that he would probably try to avoid his creditors whenever possible.
Regular references to 20th and 21st century pop culture may seem odd when the comic is set 500 years in the future... until you realize how many common phrases used today come from Shakespeare's plays it wouldn't be surprising that the same would happen with modern entertainment.
Here Florence is talking with her mouth shut, and she reveals later that she learned to talk using ventriloquism, as it helps a species without lips pronounce various sounds better..
The Theme Naming of the robots Edge and Blunt! Edge is smart, abrasive to people and sharp-witted, Blunt thinks and speaks slowly due to hardware problems, has nothing but the public good in mind and is so devoted to being Three Laws-Compliant he wants to enact Genocide from the Inside.
The police robots that come for Florence lament that they were warned about the false transponder trick, and still fell for it. Maybe because all the previous times the trick was pulled, it was a robot replacing their own transponder. They knew Florence didn't have a transponder to replace, and overlooked her not because she had the wrong transponder, but because she had a transponder at all.
One would imagine Henri the distracting ninja would be himself distracted that his target is a talking wolf in an evening gown. Except, the robot employees had greeted Florence earlier, so he already knew and had prepared himself. (incidentally, this should have tipped off Florence and Winston, since in all other circumstances a stranger would be boggle at her. Distraction successful!)
Nobody knows how long Sam's species lives, because no Sqid has ever lived long enough to die a natural death. Sam is already considered old by his species' standards, so he could die at any moment.
Florence's theory on why All Girls Want Bad Boys; I see it as a genetic gamble. Its harder to raise a child alone. But if the child is a boy who grows up like his father, the mothers half of the genetic code is distributed far wider than if she had followed the monogamous model. Good theory, and it even explains why there are so many Bad Boys prowling the planet. The Fridge moment is this; If that theory is true, it's not that much of a gamble at all. By conceiving a child with a Bad Boy, her genetic legacy is all but assured; most women will cooperate in conceiving more Bad Boys with her sons, and there's a whole world-full of Bad Boys to sire grandchildren on her daughters. Project this both backwards and forwards and you realize this is why so many Humans Are Bastards.
This is actually supported by the Trivers-Willard hypothesis; females in poor conditions have more female than male children, while females in comfortable conditions have more male than female children. Thus, the children of comfortable(IE wealthy) parents always have their choice of females to impregnate. In pre-industrial times, that meant the children of warlords. And females that submitted to them were more likely to be placed in comfortable conditions to bear males. Feel free to throw up.
All the humans who have seen what Sam looks like under his environment suit have been horrified and disgusted. All the non-sapient Earth-descended animals that have seen what Sam looks like under the environment suit have the overwhelming urge to try to eat Sam. Imagine what it would be like for a person who understands that Sam is also a person to suddenly and overwhelmingly want to eat him anyway.
When Clippy appears before court, he's asked if the plan to give Mr. Kornada all that wealth was the only solution available under those constraints. He replies that no, it wasn't the only one: but it was the plan with the highest chance of the planet's survival. Clippy had considered and discarded at least two more, and was held back only by his own morals. That one instance differentiates the AIs on Jean from a mere paperclip maximizer.