Pretty Woman (2013)
Pretty Woman was the first long-form short film I ever made when I was attending SAIC. It's a parody on romantic comedies and a gender-bender about a young boy who falls in love with a trans man (or a crossdresser, the trans community wasn't as polarizing back in 2013 as it is nowadays). The fact that the boy falls in love with a man is mostly a punchline, but in summation, the film is about allowing yourself to be vulnerable and accepting who you love, even if they aren't who/what you originally thought they were.
As mentioned, this was made back in 2013 and it's quite aged, but I can't help giggling every time I watch it. The audio is terrible and difficult to understand at times, but for me it landmarks a turning point in the way I approach making videos.