Lost Holiday seems to fancy itself some sort of crime drama or buddy comedy. I’m not saying that it’s neither, but it does seem to suffer from a lack of passion in its characters, just as those characters suffer from a lack of passion for their own lives.
Margaret (Kate Lyn Sheil) and Henry (co-writer and co-director Thomas Matthews) are home in D.C. for the winter holidays, a long way away from their lives in NYC. The thirty-year-old layabouts seem to think that their grown-up friends are lame, with their mortgages and careers. Granted, Margaret is in school to be a social worker, and Henry seems to be fine doing whatever it is he does. And who can’t relate to the alienating feeling of realizing they can never truly go home again?
Amidst the week of partying, doing a healthy quantity and variety of drugs, and not much else, a socialite and influencer (Ismenia Mendes) goes missing. Margaret puts two and two together when she realizes that they have some very loose connections to the missing woman and that they might be uniquely positioned to find her. From here, the hunt is on for this woman. That is, when Margaret is not trying to get back together with her now engaged ex (William Jackson Harper from The Good Place).
Small pockets of Lost Holiday deserve some admiration. The relationship between Margaret and Henry is fun to watch. These old friends seem to have a natural and at times hilarious rapport, and the film shines when the two of them spend time together. The film’s DIY aesthetic not only matches the characters’ relaxed approach to life and kidnapping investigations, but it feels comfortable. The world created by Lost Holiday is easy to settle into. Sheil (You’re Next, Brigsby Bear) brings a depth and warmth to her character, even when she’s morally questionable and self-indulgent.
Beyond these few qualities, Lost Holiday leaves us with a bumbling plot, a big heaping pile of white privilege, and the impression that it somehow thinks we would be interested in watching these characters party night after night. Margaret has some character arc and development, but not enough to make it beneficial for us to watch her and Henry’s excesses. The sleuthing feels tacked-on and incongruous to their holiday plans. This is no The Big Lebowski, and it’s tedious when it attempts to be.
Lost Holiday has a quick running time (78 minutes). However, in that short time the film becomes easily distracted by what doesn’t work, at the expense of what does.