Over the past decade, Ben Stiller has displayed a propensity for producing blockbuster comedies, and Along Came Polly is a fun and enjoyable comedy. Although not on the hilarity level of There's Something About Mary, Meet The Parents, or Zoolander, Along Came Polly is nonetheless a funny film (and it's certainly better than the horrid Duplex fiasco with Drew Barrymore). Ben Stiller again plays the role of the nice guy, but this time with a neurotic twist. As a result, the audience still likes his character, just perhaps not as much as some of Stiller's previous roles. But with some hilarious comedy sequences and good one-liners, Along Came Polly manages to keep its viewers entertained quite nicely.
Ben Stiller plays the role of Reuben Feffer, an insurance man who avoids risk in every aspect of his life. Measuring everything from the probability of falling through a sidewalk grate to the odds of a piano falling on one's head, he calculates every decision he makes. Following his wedding to Lisa Kramer (Debra Messing), Reuben is devastated when (avoiding the risk of scuba diving), he catches his new bride having an affair with a scuba instructor on their honeymoon. Forced to reevaluate his life, Reuben determines that he needs to take on more risk in his life.
With the help of his friend Sandy, Reuben gets out into the public arena once again, where he runs into former junior high school classmate Polly Prince (Jennifer Aniston). Polly is the exact opposite of Reuben in almost every way, and he decides to pursue her so as to have more fun in his life. Everything goes well until Lisa returns hoping to win Reuben back, and Polly discovers that Reuben ran a risk analysis on their relationship, determining that Polly was a good risk to take. Now Reuben must decide what to do with his life.