Entanglement walks a fine line on several fronts. On one hand the film is a romantic comedy that plays into the well-worn manic pixie girl tropes. On the other hand, it is a film that also wants to take a serious look at the nature of mental illness. Ben (Thomas Middleditch) has been in a state of depression since his marriage fell apart. After a failed suicide attempt, Ben discovers that his parents came close to adopting a little girl prior to him being born.

Believing that locating his almost sibling might hold the key to unlocking where his life when wrong, Ben enlists the help of his neighbour Tabby (Diana Bang) to hunt down the mystery woman. As luck would have it, his search leads him to Hanna (Jess Weixler), a free spirit who feels that life is meant to be lived to the fullest. As the two spend more time together, catching up on lost time, Ben finds himself falling in love for the first time in a long time.

For a good portion of the film, director Jason James’ film plays like a conventional indie rom-com. One that ask us to feel for the slightly eccentric Ben, though never convincing us why. The quirky humour defuses the seriousness of his suicide attempt and sets the stage for a seemingly conventional romance. However, the film takes a shift that, much like the main character itself, occasionally feels at odds with itself.

Although James presents subtle hints throughout, the tonal shift will be the make or break point for viewers. The latter half of the film features several intriguing ideas related to mental illness and depression. Thought the overall execution of these ideas feels somewhat problematic. It will be interesting to see whether viewers familiar with the various facets of mental illness will find Entanglement‘s approach charming or insulting.

Fortunately for James, his cast is more than capable of riding the rocky waves of the film. Thomas Middleditch is convincing as the confused and lonely Ben, and Diana Bang is strong as the loyal friend Tabby. Jess Weixler it the key player her though. As Hanna, Weixler gives a wonderful performance that demands the audience’s attention. She confidently navigates a delicate set of emotions while simultaneously selling the key turns in the narrative.

Despite its whimsical premise, Entanglement aims for something darker and more complex. Its success completely depends on whether one feels James’ approach to mental illness works within the film’s comedic packaging.