It's treated as a Awesome Moment for Brett that he did 38 weeks of fraternity hazing in case he wanted to join every Yale fraternity, and he uses it to help get himself and Reagan past Secret Service while establishing him as being Made of Iron and Too Kinky to Torture. "Blue Bloods" has him reunite with his frat bros...who ended up seeing Brett as a joke and Professional Buttkisser rather than a friend.
All the heartwarming moments between Reagan and Rand from "Buzzkill" and "Mole Hunt" ultimately become harder to look back at when the season one finale revealed that Rand was erasing Reagan's memories of her only friend so she would continue to focus on her studies and was ultimately just using her as pawn to regain control of Cognito Inc.
On that note, in "Mole Hunt" specifically, Reagan is forced to choose between her friends and her dad, and she chooses her dad. The finale would ultimately show that, whatever their faults, her friends do care about her, whereas even if Rand does care about her, it's as a tool first and a daughter second.
And again, "Mole Hunt" has Rand proudly proclaim "#RandInnocent" as a joke. While he is innocent of what they were accusing him of, even by Cognito's standards, he is a horrible person.
On that note, Reagan coming within a hair of erasing Rafe Master's memory of every woman he has every dated in "Ghost Protocol" is a bit more uncomfortable considering Rand did erase her memories of someone (that being her best and only childhood friend).
In the episode "Clone Gunman", as part of the cover up for the ROBOTUS fiasco, Glenn says he had to "reheat the cold war". Only a few months after season 1 released, not only would Russia launch an invasion of Ukraine, but as a result, a very long list of companies pulled out of or pulled support for Russia, one of which being Netflix itselfnote see here for a list of companies that pulled out as of early March 2022.
In the first episode of season 2, Reagan calls Rand's takeover of Cognito Inc. "the most damaging mid-life crisis since Elon Musk". At the time the season was released, Elon Musk had recently bought Twitter and made a series of decisions that were widely considered to be running the site into the ground, including firing most of the staff (allegedly targeting people who criticized him).
In another case of the Production Lead Time causing a joke to come with far more baggage than planned, while under the effects of deep Catholic guilt, Ron confesses to have been the one to tell Kanye West about politics. By the time part 2 came out, Kanye went from making a handful of odd and problematic comments to becoming a full-blown anti-Semite, accusing Jewish people of running the world from the shadows and praising Hitler, comments that got increasingly aggressive culminating in friends and business partners cutting ties with the rapper, as well as him announcing his intention of running for president with noted white supremacist Nick Fuentes as a member of his crew. Even worse, when Kanye proclaimed his antisemitic and pro-Nazi views during an appearance on Infowars, Alex Jones, who the show had mocked as a loathsome, delusional loser in "How Reagan Got Her Groove Back", was horrified and tried to get Kanye to take his comments back.
In "Brettwork", Brett laments that political scandals don't seem to destroy careers anymore and Alpha Beta says that people don't seem to care as long it's "their guy". Only about a month and a half before part 2 dropped, then senatorial candidate Herschel Walker was accused of pressuring two of his ex-girlfriends into getting abortions despite claiming to be staunchly anti-abortion and largely didn't lose any support from the GOP or his base. Noted radio host Dana Loesch even infamously said "I don't care if Herschel Walker paid to abort endangered baby eagles, I want control of the Senate".
