Along Came Polly
Reuben Feffer (Ben Stiller), a life insurance underwriter, is celebrating his honeymoon with newlywed wife, Lisa Kramer (Debra Messing), on the island of St. Barts, but catches her having sex with Claude (Hank Azaria), a French scuba instructor. Returning home to New York alone, he attempts to piece his life back together. Reuben goes to an art gallery with his friend, Sandy Lyle (Philip Seymour Hoffman), where he runs into former junior high school classmate Polly Prince (Jennifer Aniston).
Reuben and Polly begin dating, with her introducing him to activities he once wrote off as "too risky", such as eating at a Moroccan restaurant and salsa dancing, which culminates with the pair enthusiastically having sex together, with Reuben shouting "50" as he orgasms. The contrast between their two personalities is a source of comedy throughout the film until Lisa returns and tells him she wants to reconcile their relationship. Meanwhile, Sandy, a self-centered, former teen idol, is trying to make a comeback by having a documentary filmed about his starring role as Judas in an amateur production of Jesus Christ Superstar.
Reuben is torn between the free-spirited Polly and the safe and familiar Lisa. To solve this issue, he enters information about Polly and Lisa into a computer insurance program which measures risk. The computer tells him that, despite his numerous blunders with her, Polly is the best choice for him. Polly joins Reuben on a sailing trip where he is to inspect Leland Van Lew (Bryan Brown), a high-risk client, but she is offended when she sees his risk analysis of her. She rejects his proposal to move in together, telling him that he would be better off going back to Lisa.
Back home, Reuben tries talking to Polly, but to no avail. He eventually invites Lisa to Sandy's opening show, where he learns that Polly is leaving New York for Cincinnati in a few hours. After a speech given by his father, Irving (Bob Dishy), to Sandy about not living in the past, Reuben realizes he wants to be with Polly and not Lisa, and he rushes to her apartment to stop her from leaving. Polly is not convinced she should stay with him, so Reuben eats food off the ground to prove he is capable of taking risks.
Reuben and Polly vacation on the same beach where Lisa and he had their honeymoon. Reuben again encounters Claude, but instead of being angry, he thanks Claude before heading into the water with Polly to join Van Lew on his new boat.
bleak, comedy, entertaining, storytelling