How to Lose Your Lover is a quirky and cynical romantic comedy born out of a sitcom plot and rife with offbeat characters. Directed by Jordan Hawley, the film has a familiar charm that lends itself to the grand tradition of cute-yet-sarcastic comedies, never delving too deeply or making too big a splash. It also happens to be a rare example of a mainstream release that features a lesbian relationship in a completely nonchalant way, which in this case is both a good and a bad thing.
The plot follows Owen (Paul Schneider), a writer with a long history of failed romances (including one with the city of LA) and a job penning overblown biographies of B-list celebrities. He decides to “break up” with his life, burning bridges with his friends and setting off for the east coast, to write a biography of a Russian physicist. Just before he boards the plane, he meets Val (the fantastic Jennifer Westfeldt of Kissing Jessica Stein), and he decides to stay, temporarily. He then puts their new relationship into warp speed, trying to sabotage it with too much honesty.
It's all rather gimmicky, but Hawley plays it smart, delivering some truly amusing scenes, not the least of which is Owen's reluctant return home after meeting Val. He climbs into his own bed only to find Allison (Poppy Montgomery of Without a Trace), his housemate, best friend, and former lover; in bed with Stephanie (Tori Spelling, of Beverly Hills 90210 fame), another of his friends. The three of them share a wonderfully awkward moment trying to decide what Owen should do with his life.
The film presents the Allison/Stephanie subplot in a positive way by showing Owen's casual reaction and easy acceptance of their relationship. He's even inadvertently responsible for hooking them up, as he tells Stephanie of Allison's long ago interest in her at his farewell party. Throughout the film, Stephanie continually asks Owen for advice (since he knows everything about Allison and what impresses her), and he delivers readily, wanting his friends to be happy together.
Tori Spelling is hilarious as Stephanie; a party-loving lesbian seemingly taking fashion cues from a 90's era Gwen Stefani. Stephanie also happens to be the “giver” in the relationship, lavishing gifts and getaways on Allison.
Allison is more of a mystery; it's not even made clear whether she is normally attracted to women or not, though her encounters with men are numerous and well documented. However, her character never comes across as being wishy-washy; she knows what she wants, and has no pretenses about being in a giant romance. When asked whether it's “the real deal” with Stephanie, she pensively sips her tequila and states “I don't know. I'm having fun, and besides, we have more in common than I thought.” Owen simply replies “Well, I'm glad you're happy.”
Owen is more concerned about his romance with Val than anything, and he puts their relationship on “the fast track” meeting her parents immediately and showing off his every flaw in attempts to test their potential. His theory is that “it takes three months to really get to know a person, I don't have that time!” and he wavers between moving away and half-living in the same house, though his room and bed have been taken over by Allison and Stephanie.
The movie borrows heavily from the plots of American Beauty and How to Lose a Guy in 10 Days, showing aspects of Owen's complete detachment from his life, and his attempts to drive Val away with his least attractive qualities. These sequences are undoubtedly the funniest and the most successful in the film, from Owen's hilarious encounters with Bucky, the former astronaut (and utter moral vacuum) angry about his half completed biography; to Owen's insistence on visiting Val's parents on their first date.
This is where Lover truly shines, when it combines sight gags (like Owen creating a panic-inducing “earthquake” at a party) with pure situational comedy (Val's incredibly quirky parents loving Owen's candor, much to his dismay). In one of the very best sequences of the film, Owen spikes the champagne at Val's charity dinner with ecstasy, resulting in one incredibly friendly group of older folks, raving on the dance floor and happily giving to Val's cause.
But the film isn't without flaws. Besides the conceit of the central plot, a great deal of confusion surrounds the characters and their true motivations, especially in its final third.
Predictably, it's revealed that Allison still has feelings for Owen, and a sort of odd love triangle forms between Val, Owen, and Allison, with Stephanie left somewhere on the sidelines. At this point, the film becomes rather muddled, and the audience wonders where Stephanie fits into the picture. The entire ending of the film is confusing and unsatisfying to say the least, and it's difficult to swallow the abruptness of it all.
Taken as a whole, How to Lose Your Lover is a flawed, but very funny film. It contains many laugh-out-loud moments, with some great performances from Westfeldt and Montgomery, not to mention a fun turn from Tori Spelling. It's easy to write it off as a goofy romantic comedy, but its light touch and fun moments make up for the uneven writing at the end. It's very much like its central character: lightweight, and rough around the edges, but ultimately worth the time.