It was supposed to be the best time of his life, but it turned out to be a nightmare for Reuben Feffer, played by Ben Stiller, as he catches his new bride being unfaithful to him with a scuba instructor, on their honeymoon in St Barts. After returning home by himself, feeling dejected and alone, Reuben meets up with Polly Prince (Jennifer Aniston), who is a former classmate from school, and they develop a relationship. The two hit it off right away, as his new flame begins to open his eyes to new possibilities, which he would not have attempted in the past. His former wife Lisa is back with aspirations of a second chance with Reuben.
Reuben decides to assess each woman and see which of the two would be less of a risk for him to continue dating, in order to do this he must use his computer and plug in their information to see what his risk assessment program would spit out. The software program is designed for insurance purposes, but Reuben believes that it will work for this particular scenario. There is a history of unexpected blunders with Polly, but as the computer suggests, Polly is the better choice for him. Reuben decides to take Polly along on a sailing expedition as he went to visit a client, but she discovers the assessment and is very offended.
Reuben decides that there is no need to inspect his assessment any closer, he also realizes that his emotions are steering him towards Polly, and despite the fact that she is getting ready to leave him altogether, he rushes to try and save the relationship. After his computer assessment was completed, Reuben decides to ask Polly to move in together, which she determined was not a good idea. John Hamburg writes and directs this Comedy romance story that stars Hank Azaria as Claude, Debra Messing as Lisa Kramer and Alec Baldwin as Stan Indursky.