The Lifeboat (2009)

Paul is a New York City office temp approaching 30. Due to his intense fear of the singles scene, and his effort to avoid it at all costs, he has bounced from one unfulfilling relationship to another. While trying to find a way to escape his current relationship, he is unexpectedly and unceremoniously dumped. As he tries desperately to revive the relationship in order to delay the inevitable, his lothario best friend Gil forces him to confront his biggest fear; the New York City singles scene.