Awkward high school junior. As Josephine occupies the lead role in this BMC genderbend, with parts in nearly every song, the voice-actor for Josephine must be not only a strong singer and actor, but also very dedicated to this project (although deadlines shouldn't be an issue, you'll need to be willing to put in a lot of time). I imagine Josephine's voice to sound gentle and amiable, but you can't quite lose that awkward-Jeremy-vibe. However, this is just how I imagine it; it's fairly up to interpretation.