Reuben Feffer (Ben Stiller) is a nice Jewish boy who has just married the love of his life, Lisa Kramer (Debra Messing).  While on the first few days of their honeymoon, a nudist scuba diving instructor (Hank Azaria) seduces his new wife and poor Reuben returns home heart-broken and alone. A chance encounter with a happy-go-lucky old school friend Polly Prince (Aniston) sparks a change to the overly-organised daily routine of this life-insurance analyst, and things are finally going well for Reuben until one day Lisa shows up at his flat - begging for another chance.

Just like that scene from Friends, Jennifer Aniston spies a comparison chart on the boyfriend's laptop, and decides to make his decision easier by walking away.
  Stiller comes to his senses, tells the ex what he thinks of her, and then goes to win Polly back before she skips town again.  He's in luck because she forgot her weasel(!), so when she returns to the old apartment he proves his love for her by eating a peanut off the sidewalk. It's a long story.
  Meanwhile his best friend Sandy gives the performance of a lifetime to convince the board to give the crazy Aussie bloke life insurance, and the film ends with Reuben and Polly on the same luxury beach as the early scene - but this time turning down Claude the creepy French scuba diver's offer of some private 1-1 lessons. Wise move, Reub.