would connor and tom actually work as a couple?
Got this a while ago (sorry my inbox is. a mess.) but I HAVE been thinking about it kind of obsessively ever since so I'm gonna answer it now. Here's how I think it would go:
They move to Connor's New Mexico ranch and bake bread and (badly) ride horses and both think of themselves as much better ranchers than they actually are. The ranch is decked out in Napoleonica and Ancient Roman artifacts. They live in romantic bliss for a while, throwing big romantic gestures at each other. Tom slowly starts to go batty like Jack Nicholson in the Shining because he doesn't have any subordinates to punch-bag and he never gets to wear a suit anymore and despite what he says about sheep farming or whatever he's always been a pretty ambitious career-oriented guy. Connor tells Tom he wants to run for President and Tom KNOWS this is not a good idea but he's thisclose to putting an axe through the front door for fun and he needs a project so he tells Connor to go for it and makes himself Connor's campaign manager. Tom becomes obsessed with winning despite Connor's batshit policy platform (which they end up having several fights about because Tom wants him to change it to something moderately palatable to the public). He engages in several strategies of dubious ethics and legality to get some of Connor's key opponents to drop out until he actually has half a shot in the Republican primary. He's going up against Mencken. He fucks the debate so bad that Tom decides to run a smear campaign against Mencken only to discover that they've spent all their money. (Connor's funds only came from Waystar stock dividends and Tom hasn't been working). They are Flat Broke. Tom leaves in the middle of the night and moves back in with his parents in Minnesota. Connor drops out of the race.
Tom gets a job doing accounting for a local business that he fucking hates and gets a mediocre apartment that he also hates. One day Connor shows up at his mediocre apartment and tells Tom that he misses him and he still loves him etc and then he proposes right there and Tom is so blown away by the gesture that he accepts without considering whether this is actually a good idea. They will get married at Lake Como (Minnesota edition). Connor starts spending all of the money Tom is earning at his mediocre job because he has no idea how to live as middle-class and it puts strain on the relationship. GoJo buys Waystar (which kind of comes as a surprise because neither of them knows what the fuck is going on ever) and suddenly Connor has 3 billion dollars and they aren't "poor" anymore so they never address the strain on the relationship. They move back to New York and buy Logan's apartment from Marcia and Connor asks Kendall to give Tom a job so Tom has "something to do". Kendall and Roman make Tom COO because they need a new one now. Long hours late nights etc Tom ends up having affairs with both Ken and Roman (separately). Connor has no idea because he's too busy sitting at home trying (and failing) to learn how to carve marble so he can make a life-size statue of Napoleon. Tom feels so guilty about it he tries to throw himself in the Hudson but he jumps from a place way too low to cause any injury at all. He gets fished out and they call Connor because Connor is his emergency contact and Tom tells him he slipped but Connor knows better (although he doesn't know why). He decides to try and carve a life-size statue of him and Tom instead to unveil at the wedding.
They get married at Lake Como (Italy edition) and leave for their honeymoon on a small boat. The boat hits a rock and capsizes and they both drown. Their bodies wash up on the Italian coast clinging to each other. All three Roy siblings forget to go to their joint funeral
