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My name is actually Jessica "Jessi", but even so, I adore Jesse on a boy (not like I could ever use it, though). Jesse is a rugged, handsome, masculine name; Jessie is entirely unrelated. Sweet, pretty, and feminine without being frilly. Though they sound the same, they both give me completely different mindsets, as they are separate names. Jesse is very nice, and I wouldn't worry a bit about the similarity to Jessie.