The disastrous email in question is sent by neurotic Los Angeles dweller Wesley (Nasim Pedrad, “Brooklyn Nine-Nine,” “Saturday Night Live”), an out-of-work, motor-mouth guidance counselor in desperate rush to land a job and launch into a relationship with an ideal guy. Living in the trendy Echo Park neighborhood with seemingly unlimited resources (as evidenced by her well-appointed apartment) like her two best friends Kaylie (Sarah Burns) and Brooke (Anna Camp), the thirty-something Wesley goes from blind date to dead-end blind date, collects information about freezing her eggs, mourns over her dead birds and takes pride in being different. She defines herself as “an acquired taste,” except in reality, she just can’t be bothered to think situations through and say the right thing at the right time.
Take, for instance, her unsuccessful job interview at the start of the film which introduces us to Wesley with a generous side of weapons-grade cringe. In an effort to sell her credentials to a well-meaning nun about why she would be the right fit to guide their young Catholic School students, Wesley brags about her lack of experience in the field and talks about masturbation in great detail because … well, she is such a Samantha and that’s just one of her adorable quirks, to sabotage a job interview with small talk on self-pleasure. Thanks to her reliably off-putting lack of filter, Wesley also messes up a date soon enough with Lamorne Morris’ charming Sean; a bit of a mansplainer, yet still, pretty much the only character in the film that resembles a real human being. Understandably yet curtly, he cuts their rendezvous short.
Enter Jared (Robbie Amell), Wesley’s next romantic interest and enthusiastic bedfellow around whom our hopeless un-dateable decides to become an entirely different person (e.g. act like a grown-up who doesn’t always say the first thing that comes to her mind). But after not hearing from Jared for days on the heels of a great date and even better sex, Wesley, along with Kaylie and Brooke, decides to take matters into her own hands. She sends a humiliating, certifiably crazy email to Jared, only to find out moments later that he had been in an accident and stuck in a hospital in Mexico, somehow without access to his electronic devices. Already dreaming of a future of being happily married to Jared, what else could Wesley do if not travel to Cabo, break into his resort suite, and delete the email?