NOTE: This spoiler was sent in by JDoby ...
The movie starts with Reuben (Ben Stiller) and his friend Sandy (Philip Seymour Hoffman) getting ready for Reuben’s wedding to Lisa (Debra Messing). All seems perfect until they go on their honeymoon. Our newlyweds meet up with a buck-naked scuba instructor on the beach offering them scuba lessons and Lisa seems to be all for it (all for the manhood of the scuba guy rather) whereas Reuben is definitely not hip on the scuba idea. But, being the good husband Reuben lets Lisa go scuba diving alone with the instructor while he gets their hotel room all spruced up for a romantic evening.
Reuben then comes back to pick up his wife Lisa who he finds getting banged furiously by the scuba instructor. Lisa (beast of a bitch that she is) acts like this should be understandable and tries to make it seem like it just happened and was not planned
. They are on their honeymoon for god sake!!!
Reuben leaves on the next plane out and Lisa stays to live with the scuba instructor.
Torn to pieces, Reuben decides to take things on more cautiously then ever, after all he is the top risk assessor at the insurance co. he works for. Reuben returns back and everyone knows what happened which makes him feel smaller than life and he looks to his friend Sandy for support.
After a 2 on 2 basketball game where Reuben gets smeared by the big fat guy (as you see in the trailer), Sandy offers to take Reuben to an art party; it is at the art party where Reuben bumps into Polly (Jennifer Aniston), who is catering for the party.
Reuben is very attracted to Polly. He looks her up in information and calls but hangs up; he then hangs out by her apartment and pretends to bump into her and finally gets her out on a date.
They go to an ethnic restaurant where they eat spicy food (which Reuben cannot take do to his bowel problems) but he does it for her and sweats the whole date on account of the food while watching Polly eat with her hands. They go back to her aptartment and he ends up destroying the bathroom while attempting to flush down the loaf he just laid in the toilet and only makes matters worse when there is no toilet paper so he uses a hand towel and Polly’s prize lufa.
Despite the horrendous first date Polly asks Reuben out to dancing. Reuben cannot dance for anything so he gets bested by Javier, a latin dancer, who dirty dances with Polly which sends Reuben into a jealous frenzy and he tells Polly he wants to leave (without her). They argue and then Polly takes him back to her place for some sex
After that Polly & Reuben start to hang out more and more. They have another episode at the dance bar and Reuben has it out with Javier in the bathroom where he tells Javier to stay away from Polly; Javier reveals he is gay and then Reuben asks him to give him dance lessons which he does. Reuben then has his dance finale at the dance club to show Polly he cares for her. When things start going well in the relationship all of sudden they come back to Reuben’s place and Lisa is there telling Reuben she wants to come back. Polly freaks and leaves the two alone and Reuben actually contemplates the idea of taking Lisa back.
Reuben takes Polly out on a sailing trip with a client from the insurance co., Leland, a reckless old fella who lives life to the fullest, almost too much. Reuben is assigned to make a risk assessment on to see if his insurance company can make a policy for him. We learn that Reuben has decided to put both Polly and Lisa into his risk calculator program to see who is the safer choice. During a storm at sea, Polly plays with Reuben’s laptop and accidently finds the risk program which has chosen her as the safer companion. Polly, now pissed off, tells Reuben he is too straight and narrow for her and that she likes to take things day by day. She also reveals that her dad had lied to her and that he had a family in two different cities and that impacted her life so much that she cannot commit to anything. She tells Reuben to get back with Lisa since she is more suitable for him.
Polly decides to leave town but before she does Reuben finds himself at Sandy’s play with Lisa which Sandy wrecks by refusing to play a lesser role than he feels he deserves and then Reuben’s dad puts everyone in check by stating: It’s not what you do in life but whether or not you have fun while you are doing it. And that a lot of times something really good comes your way when you aren’t expecting it and you need to take those chances. After that speech, Sandy comes to grips with his acting woes and agrees to help Reuben get back Polly. Reuben confronts Lisa telling her what a cold bitch she is for her escapade on the honeymoon and races off to catch Polly before she leaves town. He makes it to her aptartment to find she has left but forgot her pet ferret (which is blind and provides some comedy in the film).
Soon, Polly comes back looking for her ferret and sees Reuben. They make up and he proves to her that he is willing to take a chance and start living life rather than being so anal.
The movie ends with Polly and Reuben on the beach at the same resort of his honeymoon and the same scuba instructor approaches Reuben upset about Lisa leaving him (rather than Reuben) and asks Reuben if he wants to go scuba diving. Reuben replies yes but with Leland, who has started up a scuba diving business at this resort after getting approved at Reuben’s insurance co. to get a policy.
Polly admits they are not married but she is at least more than a girlfriend to Reuben (which is a big step for her) and Reuben gets up to reveal he is naked on the beach as they head into the water and kiss.