Unlucky in Love
2023 · 5m · USA
Directed by Rachel Handler, Catriona Rubenis-Stevens
Genres: comedy, musical, romance
Tones: tender, theatrical, whimsical
A flash mob planner falls in love with a singer over three years of ups and downs, all in and out of song.
Picked by Margot
The scouts
A flash mob planner + singer rom-com is exactly the kind of gilded premise that usually makes me roll my eyes, but Handler and Rubenis-Stevens are doing something weird with the theatrical constraint—let me know when this plays so I can explain why I'm wrong about it.
The three-year structure paired with the musical form creates a genuine formal argument about how song and time compress emotion; this is a short that knows its debt to mid-century musicals while interrogating what it means to make art from romantic failure.
The decision to let the performers sing live through the awkwardness—no studio overdubs, no cinematic gloss—makes every flubbed note and genuine moment land with actual stakes that a polished version would've sanded away.