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safe2276488 artist:assasinmonkey868 spike95390 twilight sparkle372436 alicorn338039 dragon92468 pony1709980 g42134304 book46067 digital painting932 duo208349 female1918807 male589481 mare812578 rain8425 reading8610 sitting100770 twilight sparkle (alicorn)155353 winged spike10738 wings252634

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Calena
Roseluck - Had their OC in the 2023 Derpibooru Collab.
Tree of Harmony - Drew someone's OC for the 2022 Community Collab
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Verified Pegasus - Show us your gorgeous wings!
Preenhub - We all know what you were up to this evening~
Philomena - For helping others attend the 2021 community collab
Twinkling Balloon - Took part in the 2021 community collab.
Ten years of changes - Celebrated the 10th anniversary of MLP:FiM!

Just a cute artist
As an artist, I can tell that Assasinmonkey did it on purpose to make it interpretative, mostly in a sad way:
 
We are not watching their faces, and their body movements give us a lot of information that could be anything from sad to nostalgic, from happiness to worried, from worries to relief, so we can only imagine if they are smiling, or crying, or any other expressions (first point);
 
The background is blurred with different colors, and even though we can tell it’s part of Twilight’s castle (judging by the crystal colors in the walls), we can still assimilate with other objects, things, memories, and each person that sees this picture can find a different thing with it (second point);
 
We can see there are some books over there, but nothing more than that, to make sure we have one thing that is really important and part of their lives, however, the characters and the picture itself don’t tell us the rest of the story and what’s going on, making it up for us to decide (third point);
 
You could say it’s raining, or that there is sand falling down in their heads, or that this picture looks like it comes from an old paper, to remind a moment in the past (fourth point).
 
Overall, the desaturation, and the occult, and the “old” aspect of it, how the composition aim for the characters and their surroundings, everything makes it a sad, mysterious picture.
 
I would have a lot of trouble to decode all those interests in a picture and make them work so well together, so I can’t tell you guys how amazing this art is. Bravo Assasinmonkey!
Minus
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
King Sombra - Celebrated the 10th anniversary of The Crystal Empire!
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Non-Fungible Trixie -
Kinship Through Differences - Celebrated the 11th anniversary of MLP:FIM!
Philomena - For helping others attend the 2021 community collab
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab

Leader of the G4 purists
Is this Twi and Spike salvaging books after her treehouse was destroyed? It just looks so wet, like the book piles are not in a good place. And the backview makes me feel concern.