Hi! I don't remember if anyone asked this, but do you have any headcanons about Shermie Pines?
Ah, see, this is the part where I totally self-promote share this wonderful, totally not owned by me ask blog reply: https://askthestans.tumblr.com/post/756343677567336448/hey-stan-can-you-tell-us-stories-about-your
But here's a full summary of my headcanons on the guy:
Older brother to Ford and Stan. I know the timeline's screwy with that baby in the background of ATOTS, but I personally just headcanon that that's some other baby and Shermie's not around in the house because he's off in the military.
I definitely picture him being in the Navy. I picture he's got sailor's tattoos. And actual cool ones, no offense to Ford.
I can't find the reference for the life of me, but I swear to God I once read from Hirsch (I think it was a tweet?) that Stan learned the "you cuddle up to a girl, knock her up, suddenly your life's fallin' apart" oddly specific joke in Little Gift Shop of Horrors from Filbrick. Going with my headcanon that Shermie's the older brother, that means he's the oops baby.
Because of that, and Filbrick's general suckage, Shermie struggled a lot with his dad like the Stans did. I think like Stan, he wasn't especially exceptional - or at least in a way that could make them money like Ford's brains - and Filbrick might have projected a whole "my life fell apart after I had Shermie" thing on the poor guy. So... I don't imagine Shermie got along real well with Filbrick. I also headcanon the large gap in years between Shermie and the Stans as Filbrick's hesitation to have more kids. I think Caryn would have wanted more, and eventually convinced him to have another (and whaddaya know, two for the price of one!), but Filbrick all over just gives me the vibe of a guy that never wanted to be a father, and Shermie knew that even as a kid, so he felt rather unwanted.
In terms of personality, I see Shermie as like... a straight laced golden retriever. Like a pure heart of gold "sees an old lady struggling to walk across the street and gets out and helps her" type guy. Being Mabel and Dipper's grandfather, I think he shares Mabel's optimism but Dipper's sense of right and wrong, which is what makes him a bit of a square (see the Ask the Stans post linked above). Even so, he's not outgoing like Mabel, he's introverted like Ford and Dipper. Like... people picture introverts as moody and quiet with dark thoughts, but when Shermie's quiet he just has happy fantasies like his granddaughter, Mabel (except replace hamster balls and hot boys with, idk... probably baseball or a movie he saw one time and loved).
I see him as a family pillar of support type guy, too. As the older brother in a poor family, I think a lot of responsibility was put on his shoulders. He definitely helped run the pawn shop (though Filbrick got irritated whenever he gave too generous of a discount), and made extra money on the side for his family with a side job. Going into the military was not his choice - given the era, it was probably a draft - and he sent his money home. Caryn probably did Tarot readings on him every night between his letters home hoping they always turned up positive.
He sent little letters home to Stan and Ford, too. He'd make Stan promise to protect Ford for him since he couldn't while he was out at sea, which is what inspired Stan to be such a protector. Then, he made Ford promise to help Stan with his homework like he used to, but once again, couldn't while in the Navy. And he'd tell them about his "epic ocean adventures" to gloss over the horrors of what he was actually going through, which I like to headcanon partially inspired their obsession with fixing up the Stan-O-War so they could have epic ocean adventures someday like their big brother. It wasn't until they were older that they realized, oh... yeah, he wasn't swashbuckling with pirate ghosts in the US Navy. :(
Physically, I think he's the one who looks the most like Caryn. Stan and Ford are like Filbrick short king copy+pastes, but I picture Shermie more tall and lanky like their mother, and has her aquiline nose. Coloring-wise, he's a Pines: brown hair and brown eyes. And sailor tattoos, can't forget those.
I feel like he had to be a pseudo father-figure to the Stans because of Filbrick. Filbrick wasn't the type to teach them how to ride a bike or play a sport, scare "monsters" out of their closet, bring them home for dinner from the beach, etc. Like he fulfilled more of the emotional role of a father to them that Filbrick couldn't.
With Stan, I think he played defense for the kid against Filbrick. I don't think Shermie would have directly gotten angry with Filbrick, especially given his golden retriever-ness and the era, but he defended Stan in little ways. Say Stan broke something, Shermie might have stepped in and tried to smooth things over before Filbrick could get angry. But boy oh boy, if he saw anyone else picking on Stan (or Ford, for that matter), better watch out. He might be a golden retriever, but he's still a Pines, so he's got that whole, "Mess with my family and I'll send you to the hospital." thing going on.
With Ford, I think Shermie was like Stan to him, protecting him and generally trying to make him not feel weird for his polydactyly and nerdiness. While on the surface I think Shermie and Stan might have bonded more because they had more shared surface level interests, I think Ford really looked up to Shermie, especially since Shermie was - as an introvert - the closest to Ford in personality in their family. Shermie wholly supported his love of weirdness, even if he didn't understand what the hell he was talking about half the time, and often would go along with him and Stan on monster hunts as kids just to make sure they got home safe, even if he had no interest in the paranormal himself.
As far as flaws, I can see him having inherited Filbrick's temper and absolutely hating himself for it. Like normally he's a sweet, happy-go-lucky guy, but when he blows up he feels like such an ass afterwards because it reminds himself of his father. His golden retriever personality might have been a way of him trying his best to form an identity far, FAR away from Filbrick, so when parts of Filbrick come out, he feels gross. The Stans look the most like Filbrick, but Shermie - for as nice and sweet as he is - inherited more of Filbrick's bad personality traits than they did.
When Stan got kicked out, Shermie was out at sea and their mother hadn't told him about it, feeling awful she'd let Filbrick just kick Stan out. So when he got home, he was like, "Where the hell is Stan?", and Caryn had to tell him. Shermie always blamed himself for not being there to play defense for Stan like he always had in the past, but at the same time, he was P I S S E D that Stan broke Ford's science fair project. And given that Caryn felt guilty and didn't want to speak against Filbrick and Ford's opinions, and Filbrick is a dick, and Ford was still freshly wounded from the whole fight and disappointment... well, he got a biased view of Stan. He felt so betrayed by Stan for decades for having "hurt" Ford and the family. I think this would explain why he wouldn't have gone to Stan's "funeral" later on. Cue him feeling like an asshole after the events of Gravity Falls and Stan and Ford and/or the niblings tell their grandfather what went down the last three decades.
Even so, I think he tried to find Stan afterwards in his drifter grifter years, but to no avail. Stan didn't want Shermie to find him and disappoint him, and all the evidence Shermie did find seemed to prove what Ford and Filbrick said about Stan, so... :(
He worked in the IRS for his career after the Navy. It made Stan barf when he found out. But Shermie just wanted a good old normal family life and a boring job after what he went through in the war.
As for the way he interacts with Dipper and Mabel, just... pure cuteness. Picture the most stereotypical sweethearted grandfather. Stan and Ford are like the cool old relatives, but Shermie is the big softie old relative. He buys Mabel craptons of arts and crafts and knitting supplies for birthdays and holidays, and he buys Dipper whatever paranormal stuff or video games he wants. He fully sees Dipper as like a little Ford and a lot like his own son (D&M's dad), but he loves Mabel too, of course.
If I think of any more, I'll be sure to add them to this post. :D















