Asking Anna

Maybe marriage would be like a tumor: something that grows on you with time. At least that’s what Steven Deutsch thinks as he fingers the ring in his pocket, trying to decide whether he should ask Anna Sherman to marry him. Steven is almost thirty, going on twenty, and the future still feels like something that happens to other people. Still, he knows Anna won’t simply agree to be his long-term girlfriend forever.

When Steven flies to Seattle for what should be a routine medical follow up, he brings Anna and hits on a plan: he’ll introduce her to his friends from home and poll them about whether, based on their immediate judgment, he should ask Anna. But the plan goes awry when old lovers resurface, along with the cancer Steven thought he’d beaten, and the simple scheme he hoped would solve his problem does everything but. 

Asking Anna is a comedy, in the tradition of Alain de Botton’s On Love and Nick Hornby’s High Fidelity, about how the baggage you bring on a trip isn’t just the kind packed in a suitcase.