The protagonist of Say When, Megan (Keira Knightley), is stuck in a late-twenties rut that is somehow both a cliché and a missed opportunity. Her unfulfilling life of disappointment, peppered with understandable but exasperating decisions, is sadly echoed throughout the structure of the film itself.
Megan’s current situation of avoiding her boyfriend and refusing to commit to a career culminates in her latching on to Annika (Chloe Grace Moretz), a teenage girl, who Megan connects with due to her own arrested development. Everyone she knows is getting married, having children and rushing into the next part of their lives, while she is essentially procrastinating starting her life. The transition between the lost, uncertain years of adolescence and the supposedly stable relief of adulthood is one surely full of humour and insight, but neither is more than briefly glimpsed at in this film.
The world of Say When is ridden with failed relationships, and an acknowledgement that divorce and disillusionment are part of what we can expect from the uncomfortable but necessary process of becoming an adult. Megan is nowhere close to this maturity at the film’s beginning – she has a dead-end job courtesy of her father and friends that bring up stories and anecdotes from their own teenage years as though nothing else has happened since. It is only with an at most partially believable friendship with Annika that Megan is confronted with young adulthood at its most potent and ridiculous, and is thus able to dispense advice to a situation she can finally realise as outside of herself.
In his performance as Annika’s father, Sam Rockwell carries a huge amount of warmth and much needed humour, and retains his enjoyability despite the predictability and sentimentality that the plot musters up in the film’s final act. But despite his reliable charms and the obvious compassion director Lynn Shelton has for her characters, the film gets lost somewhere between pushing its characters into adulthood and trying to scrape together reasons why they even should. Its themes about growing up and taking responsibility for yourself would ring a little more true if these parts of life weren’t presented as so profoundly unfun.