This might be my most Controversial post and if you're someone who's genuinely rooting for tom and greg to have their happily ever after in canon then you might not want to read past this point. Just to be perfectly clear I do love tomgreg in both their canon and fanon forms and absolutely no shade to the unironic requited tomgreg truthers, you're the backbone of this fandom and I love your work etc. But. I'm still skeptical of an actual romantic relationship going canon and even more cynical about it actually ending well so, uh. Dead Dove Do Not Eat and all that

I think that Tom being unable to make a really definitive bold choice is intimately related to why I think canonical tomgreg would end in acrimonious divorce (at least with how the characters are at the end of season 3… obviously character development is real and could hypothetically shift the equation). Tom is the literal human embodiment of that fable about the kid who reaches into the cookie jar and gets a huge handful of cookies but then his hand get stuck and he can’t pull it out and he starts crying until someone explains to him that if he lets go all but one he’ll be able to get it out. Except he’s never realized that last part and he’s so afraid of ending up with no cookies at all that he can’t let them go and instead crushes them into dust and tries to eat the crumbs and goes “this is what I wanted actually. This is fine. This is what normal well-adjusted people do and I am Happy.”

It’s deeply rooted in fear and that’s because Tom’s other fatal flaw is being a little bit of a coward. I say this with utmost affection but he’s always hedging his bets and trying to make the safest choice. This is not always a bad thing, but sometimes you do have to make the bold choice just to learn things about yourself. (Or simply because it's the Morally Right Thing To Do but uh. We don't need to get into that right now re: Tom). You have to make a choice and sacrifice something in the process and that’s how you learn what will make you happy and what won’t. Except Tom is so afraid of being unhappy and making the wrong choice that he can never let himself do that, and that’s why he doesn’t really know who he is and what he wants and instead lets himself be defined by societal images of wealth and privilege. He likes expensive things because that’s what he’s supposed to like. He wants to be CEO because that’s what he’s supposed to want. I think if he actually became CEO he would be miserable, in part because of what he’d need to sacrifice to get there but also because being CEO means being bold and taking risks and I think that’s actually his own personal version of hell.

That’s part of why I’m skeptical of tomgreg going canon because I think leaving Shiv for Greg would be an incredibly bold move and I don’t think Tom’s capable of that. Maybe if his marriage fell apart Tom would go for Greg, but then I think he’d very quickly find himself in a “grass is greener” situation. I don’t think he would really actively choose Greg, internally, so much as stumble into that relationship because Greg is there and Greg is the person he’s closest to, and eventually this would eat away at him. That’s NOT to say Tom wouldn’t have very genuine feelings for Greg, but I think stumbling right from his failed marriage into a relationship with Greg would set the whole thing up to crumble and collapse, especially once the weight of Tom’s emotional baggage sets in. There’s going to be a part of him asking himself “do I really love Greg or was he just convenient,” and rather than making the decision to really commit to Greg and see if the relationship can work he’ll start developing an emotional affair with someone else without even realizing what he's doing, because the problem with really making the decision to try and commit to Greg wholeheartedly is what if it ends up being Shiv all over again? What if he decides to be vulnerable with Greg and open up to him and give Greg his emotional fidelity and Greg ends up letting him down?

And because he's incapable of having an emotionally honest conversation he just starts tallying everything Greg does in some mental T-chart of "he loves me/he loves me not". Meanwhile, I do think Greg would be largely taken in, at least initially, by the idea that Tom threw everything away for him and when he realizes that Tom's marriage to Shiv was going to crumble into dust on its own merits anyway he's going to start feeling like a consolation prize and start pulling away and that's going to make the whole situation worse. When the relationship finally breaks down it will be acrimonious because both of them are going to feel upset and betrayed and misled. And that doesn't even begin to factor in Tom's uglier possessive and abusive tendencies and the pressure that remaining at Waystar would put on the relationship and whatever unresolved issues Greg still has around his gay homewrecking dad. Theoretically, they could go to therapy and start working through this shit and improve as people and make it work but tbh I think that they're far more likely to cannibalize each other first and not in a romantic way.

I would love to see it though. I really would. It would be an absolute nightmare but it would be amazing television and I would eat that shit up. Jesse Armstrong are you listening to me. Jesse Armstrong answer my calls