Along Came Polly (2004) For the most cautious man on Earth, life is about to get interesting. Reuben, a newlywed groom catches his new wife having sex with a scuba instructor while on their honeymoon. He returns home to his life as a risk assessor in New York and runs into Polly, a junior high school friend at an art gallery. The two begin dating, and the former classmate introduces him to a number of activities he previously deemed to be too risky. After Reuben's former wife returns and wants to reconcile, he is torn between moving on with Polly and resuming a life with his wife, whom he deemed to be the "safe" option. He conducts a risk assessment, which alerts him that Polly is the better choice. Polly discovers his assessment of her and declines his invitation to move in together. Reuben must convince Polly that he is willing to take risks and that she should reconcile with him before she leaves New York.