Okay, yesterday I successfully crashed out in grief over the show ending, now I'm full on ready to put on my clown makeup until the circus ends!
I remembered my and others' theories that basically, much of Carmy's journey boils down to that he wants to ask Sydney out, but he can't, because... reasons. And I remembered this post of mine that I wrote about their little shoulder-brush moment in 4x09, and how I think after visiting Donna, something shifted in him, and he was locked in, wanting to ask Sydney out for real. And how I think when he was beginning to name some hurdles in Goodbye, he was gonna start talking about them, their relationship, but then Sydney interrupted him and talked about the menu, yelling, etc.
And well, considering all this, I've come to the realization, that in my opinion, they're one long conversation away from getting together. Like, in 4x10, they're literally arguing about what they are to each other, and they're interrupted by Richie (more on that and how it's connected to the hamachi here). They just need to finish that argument and convo.
Ebon talked about how season 5 is about people trying to work together, then we know that the car crash happens, so I think it very well could be partially about Carmy and Sydney trying to finally work together, one last hurrah before he retires, and that leads to late-night collaboration, like in the poster that we got last year. And I think it's all they need to finally work it out. Honestly, they could do it in 1 or 2 episodes, or one bottle episode, and it's done.
(Also, Richie being THE external obstacle, alongside Carmy's internal ones, that came between them in season 2 (meta here), and how he wants to be the sand who brings people together, I always thought he's gonna play a part in Sydcarmy getting together, and that still stands.)
My heart has been broken over sooo many ships over my long-long years spent in fandoms lol I can handle another one, so until that, I'm choosing to be hopeful