Plot

A buttoned-up newlywed finds his strictly organized life descend into chaos when he falls in love with an old classmate.

Reuben Feffer thinks he's found the love of his life but on his honeymoon he discovers her cheating on him with a scuba instructor. Reuben travels back home to get his life on track. On a night out with best pal, Sandy Lyle, Reuben discovers an old school friend, Polly Prince. Reuben feels a connection straight away, and tries constantly to get her to like him. But it's not going to be easy for Reuben, especially when he spends his days calculating risks, and when someone unexpected turns up.—FilmFanUK

Can a risk-averse insurance salesman on the rebound from his bride's infidelity (during their honeymoon) find happiness with a waitress he knew in junior high who's averse to commitment? Reuben is a sweet klutz who's ready to settle down but sees in her a chance to recover from disappointment and have some fun; Polly is a sweet itinerant, not ready to settle down but sees a chance to spend time with a nice guy who likes her. What will he do when his bride comes crawling back? What will Polly do, when he runs the numbers and thinks she's a good risk? Sub-plots involve his self-centered pal, who's a has-been actor, and an assignment to assess the insurability of a balls-out Aussie.—<jhailey@hotmail.com>

While in his honeymoon in a paradisaical beach, the conservative risk analyst of an insurance company Reuben Feffer finds his wife Lisa Kramer having intercourse with her scuba instructor Claude in his boat. Reuben immediately returns to New York and his friend Sandy Lyle invites him to go to a party. There he meets his former high school friend Polly Prince, who is a very independent woman that lives in the edge with her blind ferret in a cozy but simple apartment. Although having very different behaviors, they date and fell a great attraction for each other. When Lisa returns, Reuben has to decide if he wants to live his life in the suburb with his unfaithful wife, or have a risky relationship with Polly.—Claudio Carvalho, Rio de Janeiro, Brazil

Risk analyst Reuben Feffer loses his wife on their honeymoon when he discovers her being intimate with a scuba instructor. When he returns home, Reuben's friend and coworkers try to cheer him up and take him out to meet new people. He has a chance encounter with middle school classmate Polly Prince. The movie then follows the dating of Reuben and Polly, he risk-avoider and she a free spirited wanderer. When Lisa, Reuben's wife, returns from her fling with Claude Reuben must choose to take back his cold-hearted wife or run with the commitment-fearing Polly.—FMJ_Joker

Reuben Feffer (Ben Stiller), a risk analyst for life insurance, is celebrating his honeymoon with his new 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) (who was also the best man at his wedding), where he runs into former junior high school classmate Polly Prince (Jennifer Aniston). Polly's best friend is Roxanne (Missi Pyle).

Sandy tells Reuben that Polly is not right for him. Reuben thinks this is destiny and goes after her. He calls Polly but hangs up. He later hangs around her apartment, waits till she comes home (watched her eat food that she dropped on the pavement) and "pretends" to run into her. Reuben and Polly begin dating, with her introducing him to activities he once wrote off as "too risky". This included eating at a Moroccan restaurant which ends badly due to Reuben's IBS (Irritable bowel syndrome). Reuben goes to the toilet in Polly's apartment as he can't hold it any longer, but as there is no toilet paper, he uses her grandmother's stole to wipe his ass. He tries to flush it, but it ends up clogging the toilet and flooding the bathroom.

Polly likes to move around a lot, doesn't believe in long term relationships, avoids commitment and has had 8 failed relationships that ended badly for her. Luckily, Polly gives him a second chance (they also run into Reuben's parents where his mother tells Polly how Lisa dumped Reuben on his honeymoon) where they end up salsa dancing (Reuben gets jealous when Polly dances sensually with an old flame Javier (Jsu Garcia)) and later enthusiastically having sex together, with Reuben shouting "50" at the climax (he was counting down from 5 mins (as he wanted to last 5 mins), but came 50 seconds before his target time).

The contrast between their two personalities (Reuben is careful and calculated, while Polly is unorganized and random) is a source of comedy (Reuben finds that Javier is gay, gets over his jealousy and takes salsa lessons from him) until Lisa returns and tells him she wants to reconcile their relationship. She says she got tired of Claude as he only ever talked about Scuba diving. Stan Indursky (Reuben's boss) (Alec Baldwin). Sandy meanwhile is a self-centered, former teen idol, is trying to make a comeback by having a documentary filmed (with crew Dustin (Judah Friedlander) & Vic (Kevin Hart)) about his starring role as Judas in an amateur production of Jesus Christ Superstar. Sandy keeps going off script and tries to grab the limelight during rehearsals, earning the displeasure of his fellow actors.

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 least risky choice for Reuben.

Polly joins Reuben on a sailing trip where he is to inspect Leland Van Lew (Bryan Brown), a high risk client (he is an extreme sports nut) (when Reuben first meets Leland, he does a base jump in front of him and fractures his coccyx) (At the next meeting Reuben had told Leland that his company won't be able insure him and Leland says that maybe he was wrong about Reuben thinking that he would see past the risks and analyze the person. He invites Reuben to his sailboat to spend some time together) and his other best friend, 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. Leland's sailboat ends up in a storm and crashes into some rocks and sinks. Leland, Reuben and Polly have to take the lifeboat to row their way to safety. 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 in a few hours.

After a speech given by his father, Irving (Bob Dishy), to Sandy about not living in the past (when Sandy decides to play the part of both Judas and Jesus leading to an onstage confrontation with the other actors), Reuben realizes he wants to be with Polly and not Lisa, and he rushes to her apartment to stop her from leaving. Sandy encourages Reuben and says E! is not doing a documentary on him, and that he hired Dustin and Vic on his own. Reuben asks Sandy to fill in for Reuben for his risk analysis presentation on Leland and successfully grants Leland his insurance. Reuben eventually catches up with Polly and tries to persuade her to stay. Polly is not convinced she should stay with him, so Reuben eats food off the ground to prove he is capable of taking risks. Polly is finally convinced and ends up dating Reuben, but they both agree they will take their relationship step-by-step and not rush into marriage.

Reuben and Polly vacation on the same beach where he and Lisa had their honeymoon. Reuben again encounters Claude, but instead of being angry, he thanks Claude for showing the ugly truth about Lisa before heading into the water with Polly to join Leland on his new boat.