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I think it's cute but I do only like it as a nickname. But I did meet a Jessie once (not short for anything) and she was well into her 70's. After meeting her, Jessie did seem to take on somewhat of a classic charm, with the likes of names like Millie and Betsy. I may be the only one that thinks that though. I know it's mostly associated as a nickname for Jessica (a name I love).

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"LUPINWOLF: I KEEL YOU, SIRIUSDOG!
SIRIUSDOG: *whimpers*
LUPINWOLF: I KEEL YOU TOO, HARRY POTTER!
HARRY: AHHHH"
From m15m. A summary of a scene in Harry Potter and the Prisoner of Azkaban