Aselton plays Annie, while Dax Shepard (Idiocracy) plays her husband, Zach Braff. Okay, the character's name isn't actually Zach Braff, but Darren is the type of insinuating, self-consciously namby-pamby character one tends to associate with Braff. It's a more dramatic role than Shepard usually plays, and he acquits himself fairly well. Aselton's performance is also solid, but Annie and Darren aren't strong enough characters to draw us into the movie's weak storyline.
Annie and Darren are a very comfortable couple. It's clear from the opening montage that they've been living together for some time. They affectionately share time in the bathroom. They do crossword puzzles in bed together at night. They have a pleasantly intimate routine. After an awkward dinner party conversation about Darren's unsowed wild oats, the two confront the fact that they don't have sex very often anymore, and they begin to wonder if there's a problem. After wrestling with the question for a while, they decide to reinvigorate their sex life by letting each other spend a night out having a one-time one-night stand with a stranger.
Sounds like a swell idea, huh? Well, Annie and Darren are apparently morons. They're not presented as being mentally unstable or emotionally infantile, but their decision (and Aselton's temporal jostling lets us know early on that the plan doesn't go so swimmingly) is so poorly thought through and indicates such a lack of self-awareness on both of their parts that it strains credulity, and inhibits our desire to empathize. It's depressing to watch two blabbering, callow characters impetuously squander what so many strive for.
It doesn't help matters that by unnecessarily jumping around in time to the aftermath (perhaps so we'll be certain we're watching a movie and not a filmed play, but this isn't Harold Pinter's Betrayal, or Irreversible, for chrissakes) Aselton deflates a lot of the tension we might feel regarding Annie and Darren's future together.
The Freebie bears a passing resemblance to Lynn Shelton's Humpday. It shares the somewhat meandering improvisatory feel, the sporadically amusing dialogue, the presence of actor Joshua Leonard (whose co-star in Humpday, Mark Duplass, is Aselton's husband, and an executive producer of The Freebie). Both movies were shot by Benjamin Kasulke, whose video camera here nicely captures both the initial intimacy of the relationship and the harsh brightness of morning-after Los Angeles. Both movies feature a poorly thought-out, harebrained scheme devised by the two main characters. (In Humpday, two heterosexual male friends decide to make a short gay porn film together.) Humpday had a bit more of a comic edge; The Freebie is less juvenile. They both exude a sexual frankness that masks an essentially conservative point-of-view.
Aselton's movie never addresses the notion that monogamy, in fact, doesn't work for everybody, and that there are couples for whom some alternate arrangement might be better. The central couple is portrayed as so undeniably foolish that The Freebie seems to suggest that a monogamous heterosexual relationship (with babies, naturally) is the only route to true fulfillment.