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  • William says in a previous episode that his father taught him how to play piano, yet we find out in a later episode that his father died before he was born. May be too early to call it a Plot Hole though...anything is possible in this show.
  • Why the hell didn't they use "What Now?" as the Season 1 finale? It would have been a perfect note to end on. They honored William's life. The underused Beth finally had A Day in the Limelight. Randall finally forgave Rebecca. Then it ended with the cliffhangers of Kevin's L.A. opportunity, Kate's secret, Randall quitting his job, and Jack going to Cleveland. "Moonshadow" was universally panned as a horrible finale, but it probably would have made for a decent Season 2 premiere by introducing four new story arcs (The Jabecca separation, Kevin going to L.A., Kate's decision to pursue a singing career, and Randall and Beth considering adoption). That, and there would be another episode in a week. The entire season was magnificently written and produced, but the way they chose to end it is puzzling to say the least.
    • Not a justification, but it seems to go with the popular trend some dramas have been following in recent years (i.e. [series/Orange Is The New Black], [Bo Jack Horseman]) in which a season or series' penultimate episode delivers all the drama and the finale itself is seen as a "cool-down." One of the most noteworthy examples is [series/Breaking Bad] whose antepenultimate episode, "Ozymandias," is considered one of the best episodes of television of all-time and the last two episodes are, even by creators' own admissions, more of an epilogue.
  • Why did Toby's parents wait until a half hour before Toby and Kate's wedding to express their misgivings about the marriage? While they may have actually raised valid points, wouldn't it have made a heck of a lot more sense to have that conversation BEFORE the wedding was planned, paid for, and about to take place? And what would the endgame have been if Toby did leave Kate at the altar? Did his parents expect him to abandon his dog, residence, and possessions at the drop of a hat? Given that they were worried about Toby's depression resurfacing, it seems that a life-altering move like that would have been a FAR riskier decision than going through with the marriage. The speech was obviously written under Rule of Drama, but it was pretty ridiculous once you break it down.
    • Toby is established to BARELY speak to his family, and his parents barely speak to one another, so it's quite possible they have barely had time to discuss it with each other and reach a consensus until they actually saw one another for the wedding.
  • As with any show that has multiple timelines that likes to sprinkle in little plots in the past, it's bound to contradict itself at times. Some of this includes:
    • A bit of inconsistency on Beth's sibling situation. She's both mentioned not having brothers or sisters, and not having sisters, as well as growing up with at times more than a dozen people in her home, whether it was transient friends or extended family members. When we see her childhood in "Our Little Island Girl," we see that she has older siblings (brothers and a sister), but aside from Zoe, at no point does her house seem filled with dozens of extended family members and friends.
    • Randall tells William he used to sport a bit of an afro, prior to being made partner at his firm, but that he shaved it off when he got more serious about his career, shortly after Tess was born. He says that when he shaved it off, little Tess started crying, implying that she was still a baby or toddler. When we see Randall the day Tess was born, his hair is as short as it was in the present day.
  • What happens to William's old building? Randall and Beth mention it a few times during Randall's council run, but there's no mention of it during the fourth season whatsoever, and after putting out so much work to get it fixed up in the second season, it's seemingly never an issue again (especially during COVID when Randall mentions landlords and tenants having issues). Randall and Beth's New Orleans property is also never mentioned.
  • The show sometimes addresses this, but many, including critics, have wondered: exactly how famous is Kevin supposed to be? In the first season, we learn that he's been on The Manny for at least three years, making $3 million a year. But it seems increasingly like The Manny was his first/only big break after years of failure, mostly modelling gigs, student films and non-speaking parts in soap operas. Not only does it feel slightly unrealistic for someone to get a leading role on a sitcom after not so much as a high-profile supporting role, but Kevin also seemingly is one of the biggest Hollywood insiders – being on a first-name basis with Seth Myers and being able to call in a favour from John Legend – after only three years on a middling sitcom. Ironically, after his role in the Ron Howard and especially M. Night Shyamalan movies, he could believably be at the level of "Seth Myers recognizes me from half a block away on a New York City street," but at this point in the series he's almost never seen doing press tours, working with an agent or manager (does he even have an agent anymore?) or spending much time with anyone besides his family. It seems Kevin's level of fame is occasionally up- and down-graded depending on how convenient it is to get him out of a tight spot.
  • Kevin and Zoe act like they have never met before at Kate's wedding, and a few months later after months of hookups they pretend, in front of Beth, that they first met at Kate's wedding. But the flashback scenes of "R & B" show that Zoe was a bridesmaid at Beth and Randall's wedding – and Kevin was the best man. Unless the wedding party somehow didn't interact at all, they've definitely met before.
    • Eh, this is kinda forgivable. Even if you did meet and interact with somebody 15 years ago, that doesn't mean you'd still be familiar with that person if you met them again today. Their meeting at Kate's wedding could be considered more of a refreshment of acquaintance ("Oh right, you're Randall's brother" kinda thing).
  • The first year of owning a business is typically the most stressful year of anyone's life, and dance studios typically take two to four years to reach profitability. So why is it, once Clarke School of Dance opens, that Beth is always home during the evenings and not teaching at her dance studio? Of all the things in Beth Pearson's life, owning a dance studio is somehow one of the least stressful elements. And she is always home at typical teaching hours. She also comes home during school hours to tend to Tess's panic attack and says "I left the studio as soon as I could." How many classes is the studio running during school hours?
    • And just how starved was that neighbourhood in Philly for a dance studio that by March 2020 – its first year of business – Beth had amassed a large group of advanced students despite her having no known presence in the market before? There is Truth in Television that many of these dancers might have quit, but for CSOD to go from a brand new upstart with an inexperienced owner/director to a studio with large advanced classes to bleeding money a couple months into the pandemic shows a huge lack of familiarity with the dance industry.
    • Essentially, the closure of Clarke School of Dance and Beth eventually taking more of a day job at an elite academy felt more like a convenient plot device so the writers wouldn't have to explain why Beth and Randall are always home at the same hours. It also feels like a last-minute writing decision considering in the initial flash-forward that shows Beth working at a dance academy, she's shown in more of a teacher role, which she doesn't actually take.
  • In the first season finale, Stanley says that Jack is still jobless (even if he has sometimes part job). By season 5 episode One Small Step, Jack seems to have moved out his parents house. At this time, he does not know Miguel yet, so, what does he do for living and where does he live ?
  • It is never made entirely clear what Nicky’s relationship or status was with his parents after he returned home from Vietnam. Jack told Rebecca that Nicky was dead, though it’s unlikely he did so with his parents as a postcard from Stanley is seen in a box that Nicky sifts through later. Regardless, Nicky does not show up at Marilyn’s funeral, nor does he ever seem to appear around his parents post-Vietnam. It is possible he chose to estrange himself from them due to his childhood trauma and shame from the war.
  • In early seasons, Rebecca was mentioned to have a sister, but said sister does not appear aside from a childhood flashback. She is mentioned once in Season 4, but it is unknown what happened with this character. Does she have children? Do the Big Three have a relationship with her?
  • Rebecca had a complicated relationship with her parents, but she still loved them very much. So why did she not see them on her "train ride?" Especially because her love of passenger trains connected her to her father.
  • Was the show initially planning on Kate gravitating toward Gregory after her marriage to Toby fell apart? It feels so strange that they were laying the seeds for Gregory becoming a valued confidante to Kate – feeding baby Jack his first solid food, being the one she calls from the retreat and not Toby. The show had clearly been laying the foundations for Kate and Toby to split for several seasons, but considering Philip has been criticized for being a Satellite Love Interest and a Flat Character (he doesn't even have a last name!) and their romance lacking development, it prompts the question: was Gregory the original target for Kate's second love? Did COVID filming restrictions and rewrites force them to not have as much Gregory-Kate screen-time and thus they threw in this new teacher character?
  • Kevin's Seattle airport struggles – let's just ignore that he manages to break TSA rules and board without ID (since the show hand-waves it). How about crossing the border so seamlessly they don't even show it? Crossing the border can be a crapshoot during normal times – sometimes it takes five minutes, sometimes it can take a couple hours. But for Kevin to cross it seemingly instantly during the height of COVID restrictions, is absolutely wild. Technically, at the time, only people approved to cross the border could do so (technically Kevin would have been among those, since he was permitted to work in Canada, and could cross back since he was a U.S. citizen), but he still would have had to provide a negative COVID test and it would have taken much more planning than simply zipping through. It's also unclear where the car crash happens, but let's assume he was past the U.S. border so he could at least have gotten into the States without worrying about his I.D.

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