I Ship It (19:42)
IMDb; Short of the Week; YouTube; Yulin Kuang
This came out in 2014, but I didn't see it until 2018. A young woman named Zoe does a vlog (which is very reminiscent of Cyd from The Guild). She and her boyfriend, Peter, have just broken up. They used to write and sing together, but now he's doing that with his new girlfriend, Macy. (Their genre was "wizard rock," inspired by Harry Potter.) Meanwhile, Zoe's best friend, Charlie, has recently been dumped by his girlfriend, Laurel. (Charlie also has a vlog.) So, Zoe and Charlie wallow together for awhile. They try kissing, but they both claim to have felt nothing. And... Zoe decides she and Charlie should write and sing wizard rock together, and enter the Battle of the Bands against Peter and Macy. Charlie is reluctant, because he can't sing. But they do end up writing a song together called Horcruxes, which Zoe sings herself in the competition. And... the song is pretty awesome. But the competition itself isn't really important. What's important is that Zoe and Charlie are both totally adorkable, and it's pretty much impossible not to ship them. It really is a sweet and funny film.
In 2016, the short was adapted into a webseries of the same name.