Okay! The first thing I want to discuss here is that the meat of this concept is super cool. I love the idea of the different narrators and different set/lighting techniques showing who's narrating. It reminds me a little bit of the movie Hoodwinked! (which was a childhood/family favorite where four people get interviewed by the cops about a crime and each has different things to say).
A couple constructive notes: Is this supposed to be like a 'Twilight Zone' or 'Mr. Rogers' Neighborhood for adults'-ish setup? It feels very much like Jessie knows she's talking to an audience, which, if there isn't the expectation that the characters can and do talk directly to the viewer, can throw people--it threw me a little. Admittedly I'm not sure how to orient the audience appropriately in this case, but if this piece is something you want to continue working with I would experiment with different framing devices and different opening/closing scenes. Also, the way in which the older Jessie turns a corner regarding relating to the other narrators feels a bit rushed given how adamant she is about not sharing right up until that turning point.
All in all, this was kind of adorable and I think the concept is worth working with further.
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