Simon Helberg makes his directorial debut with this romantic comedy in which he stars alongside Melanie Lynskey and Maggie Grace. Quinn (Helberg) and Devon (Lynskey) are highschool sweethearts; neither of them have ever been with anyone else and their life together is content. When Quinn's colleague Kelsey (Grace) tells him that she's in love with him, the sudden realisation of never having slept with another woman dawns upon him and he tells Devon he wants to take a step back from the relationship. As he discovers what is actually out there, he realises that Devon is the only one for him and he sets about trying to win her back. The cast also includes Zachary Quinto, Alfred Molina and Ebon Moss-Bachrach.