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Description
Well, thanks to VaatiMage , I now ship Pit x Leaf. While I know very little about Leaf, the images I've seen of her make her look very cheerful and fun-loving, someone whom I believe Pit would enjoy being with. Plus, much as I love Rosalina X Pit, I feel someone who looks closer to Pit's age would be less, well, questionable.
If Pit and Leaf were a couple, I'd imagine Pit would want to become more knowledgeable about Pokemon. He seems to have a base knowledge of Pokemon (somehow even smaller than mine). And if Pit doesn't know who Daisy is in spite of his love of Mario games, he's probably not going to know a lot about any Pokemon other than Pikachu, Jigglypuff, and a few others. Fortunately, Leaf is more than willing to help Pit learn about these fantastic creatures that inhabit her world. Starting things off, she's helping him differentiate between a Squirtle and a Koopa Troopa.

Pit (c) Sora Ltd.
Leaf and Squirtle (c) The Pokemon Company

Description
Well, thanks to VaatiMage , I now ship Pit x Leaf. While I know very little about Leaf, the images I've seen of her make her look very cheerful and fun-loving, someone whom I believe Pit would enjoy being with. Plus, much as I love Rosalina X Pit, I feel someone who looks closer to Pit's age would be less, well, questionable.
If Pit and Leaf were a couple, I'd imagine Pit would want to become more knowledgeable about Pokemon. He seems to have a base knowledge of Pokemon (somehow even smaller than mine). And if Pit doesn't know who Daisy is in spite of his love of Mario games, he's probably not going to know a lot about any Pokemon other than Pikachu, Jigglypuff, and a few others. Fortunately, Leaf is more than willing to help Pit learn about these fantastic creatures that inhabit her world. Starting things off, she's helping him differentiate between a Squirtle and a Koopa Troopa.

Pit (c) Sora Ltd.
Leaf and Squirtle (c) The Pokemon Company