Holidays are usually a dice roll and that’s especially true when it comes to movies about them. The protagonist in Lost Holiday, Margaret (Kate Lyn Sheil) takes that risk. She returns to her hometown, Washington D.C. She is a woman child realizing that her high school boyfriend Mark (William Jackson Harper) is now a real adult with a bougie girlfriend.

Margaret repeats that botched reunion and its subtleties in her head. But as that happens, she realizes that she has bigger problems as she and her best friend Henry (Thomas Matthews, one of the films directors) find herself deep in a plot that involves a missing socialite.

This sounds like it can be any genre, but the Matthews brothers infuse their movie with non-sequitur humor, reflecting Margaret’s scatterbrain. There’s also a throwback feel to her screwball ways that somehow fits well here.

But as great as Margaret is, I can’t say that same about the supporting characters. Part of her and Henry’s journey into finding that missing socialite involves shady ‘executives’. And they, just like most of the supporting characters here, have one unnecessary quirk on top of another.

Margaret and Henry also spend a lot of time meandering through nondescript parts of DC, too much for a movie with a short running time and one that takes place during two weekends.

The movie’s third act also has its share of disappointing scenes. Cue the montages of Margaret and Henry’s misadventures as they try to both crack the case and party for New Year’s Eve.

Nonetheless, Sheil shines here in a role that allows audiences to actually pay attention to her. She gets to show off her versatility here. Cameos, including one from Isaiah Whitlock Jr., flesh out a movie that comes from directors with an emerging unique voice.