The only major issue keeping me from jumping on the "Wirt Pines" bandwagon is that Sara can't be Mrs. Pines. Have you considered a "Greg Pines/Uncle Wirt" AU? (I mean, we lose the fun of Wirt raising Mabel, but gain the fun of Dipper BEING RAISED by Greg.)
You know, that’s a whole separate bandwagon that a pretty fair amount of people are on (including, hilariously, Ashley Michelle Simpson, storyboard artist for Milo Murphy’s Law). Call it convergent evolution!
I approve of any train of thought that connects the Unknown Boys to the Mystery Twins, but I like my version better, for a number of reasons (spoilers for both shows follow!):
- Dipper's—and, by extension, Mabel's—resemblance to Wirt is noticeable. Neither of them resembles Greg. This could easily be explained by the possibility that they favor their maternal grandmother, but I like the directness of the connection between Dipper and Wirt.
- Over the Garden Wall appears to take place at some point in the late 80s or early 90s (note that Wirt owns a “Three Non-Blondes” tape, an obvious reference to early 90s outfit Four Non-Blondes). Gravity Falls takes place in 2012, indicating that the twins were born at the end of August 1999. It would be a bit of a stretch for Greg, who is very young during the events of OTGW (most people put him in the 5-6 age range; I doubt he’s older than 8) to be a married father by 1999; even if we are generous enough to assume that, for instance, he was eight years old in 1987, he would be only twenty by the time the twins were born. I think it’s far more likely that he was still in his teens. Wirt, though? Explicitly a teenager during the events of the miniseries. Likely well into his twenties by 1999. The timeline checks out.
- The Jewish ancestry of the Pines family. In the blended household Greg and Wirt belong to, someone, at any rate, is celebrating Christmas, as evidenced by that box of decorations in the attic—but it’s not necessarily Wirt. In fact, he takes a scissors to a Santa hat to make it into a costume. You could say “So what? He needed a hat,” or you could read it as a Jewish kid’s stubborn little rebellion against his mainstream goy stepdad. If you’re me you’re going to do the second thing.
- Here’s the key consideration, and I saved it for last because the others are easily handwaved: Gravity Falls presents us with a strange and inexplicable disconnect between the Pines family in Piedmont and their elderly relative in Oregon. It’s one of the strangest little plot holes in the series: why are Mabel and Dipper’s parents, who trust Stan sufficiently to stick their kids with him for the entire summer, completely unaware that he’s not who he says he is? Via Hirsch himself, they “thought that they were sending their kids to go spend the summer with their brilliant scientist uncle who was an accomplished scientist and a responsible man.” But if they think Stanley is Stanford, why don’t they know that Stanford was supposed to have six fingers? For that matter, why don’t the kids know about “Stanford’s” twin brother who died in a car accident? There’s a lot of cluelessness afoot and no easy way to account for it—unless you consider a divorce, an estrangement that would prevent Mabel and Dipper’s father from the kind of knowledge of his own family that he might ordinarily be expected to have. And that’s exactly the situation Over the Garden Wall presents us with: a vast emptiness in Wirt’s life where his connection to his father, and to that entire branch of the family, ought to be.
There’s more, of course. The connection between Wirt and Dipper as characters extends to more than just their appearances: Dipper’s arc is at heart similar to Wirt’s, the gradual realization (as Hirsch put it, echoing “Songs of the Dark Lantern” a little) of “a naive, self-serious, sort of socially awkward kid…[t]hat he can be the author of his own story.” Both Wirt and Dipper put on a hat and check the effect in the mirror, as a kind of signal to the audience that the journey is about to begin. Dipper echoes Wirt’s muttered “Into the unknown” with a question for Mabel: “Ready to head into the Unknown?” There’s a great deal of resonance in the possibility of these two protagonists being father and son.
I like Sara a great deal, and I think she’d be amazing for Wirt, but I’m not committed to them being endgame to the point where it’s the hill I’d die on; Over the Garden Wall takes place within a very specific bubble of time, a point in a young man’s life where he’s nervous around his high school crush, and I think the story is less about whether he ends up with Sara either way and more about whether he has the courage to ask. That said, I’ve made a point of keeping Mrs. Pines vague and I’ve seen people twist a few things for the sake of allowing Sara to be their mother, and I approve of that too. Whatever floats your boat upon your winding river.