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Description
I'm ecstatic about how this one turned out; hope you are, too. NATG's 27th day specified some sort of masquerading pony, and I knew an Edgar Allen Poe reference wasn't gonna cut it. Silliness became the next goal, and I considered pairing someone like Prince Blueblood with, say, Crackle in a mask. Also on the table was Princess Celestia dancing with this fellow: [link] ...The latter didn't go far, for obvious reasons.

Then came Derpy, and the silliness almost completely disappeared. It didn't feel right pairing her with someone or something from fanon; the "chemistry" with Doctor Whooves felt forced, and I couldn't bring myself to pick a random pony, give him/her a muffin mask, and call it a date. I wanted to completely break expectations, and I also didn't want to break Derpy's heart. I'm a sucker for romance, if it isn't obvious already.

Thus, Derpy's date became a masked non-equine, and my video-game-saturated mind narrowed it down to TF2's king of class, the BLU Spy. Nobody would be expecting him, and the situation presented would seem plausible enough to encourage both laughs and discussion; after all, people don't ask "why not?" enough. The rest clicked into place via Paint Tool Sai, and I finished the primary picture with enough time to play around with modified textures and brush settings.

"My Little Pony: Friendship is Magic" © Lauren Faust and Hasbro
"Team Fortress 2" © Valve Corporation
All rights to their respective owners, too.

Description
I'm ecstatic about how this one turned out; hope you are, too. NATG's 27th day specified some sort of masquerading pony, and I knew an Edgar Allen Poe reference wasn't gonna cut it. Silliness became the next goal, and I considered pairing someone like Prince Blueblood with, say, Crackle in a mask. Also on the table was Princess Celestia dancing with this fellow: [link] ...The latter didn't go far, for obvious reasons.

Then came Derpy, and the silliness almost completely disappeared. It didn't feel right pairing her with someone or something from fanon; the "chemistry" with Doctor Whooves felt forced, and I couldn't bring myself to pick a random pony, give him/her a muffin mask, and call it a date. I wanted to completely break expectations, and I also didn't want to break Derpy's heart. I'm a sucker for romance, if it isn't obvious already.

Thus, Derpy's date became a masked non-equine, and my video-game-saturated mind narrowed it down to TF2's king of class, the BLU Spy. Nobody would be expecting him, and the situation presented would seem plausible enough to encourage both laughs and discussion; after all, people don't ask "why not?" enough. The rest clicked into place via Paint Tool Sai, and I finished the primary picture with enough time to play around with modified textures and brush settings.

"My Little Pony: Friendship is Magic" © Lauren Faust and Hasbro
"Team Fortress 2" © Valve Corporation
All rights to their respective owners, too.