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Description
So...

His hat.
I have so many feelings and ideas about that wonderful hat. It became an association with everything that was making Dipper as depressed as he was. The first summer after Weirdmageddon, he and Wendy switched their hats back (my personal headcanon that they only wear the correct hats when they’re all back where they belong, which is in Gravity Falls), but Dipper started feeling labeled. The symbol made him feel like he had so much to live up to and so much to make up for and all at the same time reminded him constantly of the horrors that kept him up at night. So he just decided to give it up, hoping the constant reminder of being Pine Tree would leave with it. Even though he was fine seeing Wendy wear it (her way of sharing his burden), he couldn’t keep wearing it himself. It became something like a taboo. But Dip’s depression didn’t get any better either way, and I think now he’s coming to terms with the fact that it’s not his hat he hates but the downward spiral he associates with it. It doesn’t have to be that way. He was happy with it once. So he’s finally ready to confront change again, and this time change means going back to old ways.
...Obligatory sexy icon!

Description
So...

His hat.
I have so many feelings and ideas about that wonderful hat. It became an association with everything that was making Dipper as depressed as he was. The first summer after Weirdmageddon, he and Wendy switched their hats back (my personal headcanon that they only wear the correct hats when they’re all back where they belong, which is in Gravity Falls), but Dipper started feeling labeled. The symbol made him feel like he had so much to live up to and so much to make up for and all at the same time reminded him constantly of the horrors that kept him up at night. So he just decided to give it up, hoping the constant reminder of being Pine Tree would leave with it. Even though he was fine seeing Wendy wear it (her way of sharing his burden), he couldn’t keep wearing it himself. It became something like a taboo. But Dip’s depression didn’t get any better either way, and I think now he’s coming to terms with the fact that it’s not his hat he hates but the downward spiral he associates with it. It doesn’t have to be that way. He was happy with it once. So he’s finally ready to confront change again, and this time change means going back to old ways.
...Obligatory sexy icon!