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Pinkie pie is so sad
Something I would like to point out is that over time Pinkie is gathering more issues with herself. Fluttershy started the show burdened by her shyness and all the other personal monsters she has. at this point in time we see that she has cast off much of her burdens, like when she talked to Rainbow about why she wouldn't fly and situations have come up that force her to grow out of them.
Pinkie, on the other hand, is getting worse as time goes on. We see that she has DEEP issues in Party of One, but unlike Fluttershy no-one helps her with it. She just happens to snap out of it shortly after they see it. I don't blame them, but they didn't help her with it at all. She is questioning herself often, such as about being a party animal or if she's responsible or if she was judgmental. Her past definitively had a profound effect on her and now she doesn't even know it she exists anymore. And for some reason she believes her friends will forget her if she is apart from them for any amount of time.
Unlike Fluttershy, who voices her feelings unconsciously with fear and (possibly) shyness, Pinkie Pie hides her feelings behind a smile. Until someone pierces her shield of happiness she will continue to build up her bottled feelings and, eventually, explode.
I feel you captured this perfectly using one simple scene. You did a beautiful job with the expression (when I leaned closer I saw the tears and my heart nearly broke). The background is a little confusing but Pinkie is the focus of this piece. Congratulations. Keep up the great work!
(sorry for the long comment
I opened the download page and saw the soft bags under her eyes and the emptiness of the irises. A small detail that really shows her deep feelings. You are inspiring.
ave a Great Day!