Neil Diamond is the man of this film and is what brings the group of friends together, Darren Silverman (Jason Biggs), Wayne Lefessier (Steve Zahn) and J. D McNugget (Jack Black). When the group have just finished performing a song from their Neil Diamond tribute band they go to a bar to relax. A woman walks in and Wayne and J. D persuade Darren to go try and talk to her. He goes after a little more persuasion (lying) from Wayne who says she 'wants him'.
She quickly denies him and he accidently leaves his bottle of beer on the table. Another, more repulsive, man comes over to try and hit on her and Darren comes back for his beer where the woman sits him down and pretends he is her boyfriend just to get rid of the other man. They spend the night talking and eventually end up in a realtionship. However, Darren's realtionship with Judith (Amanda Peet) means he spends no time at all now with his two best friends.
Darren tries to get Judith and his friends to become aquainted and perhaps even become friends but this plan is a disaster and leaves Wayne and J. D with no Darren. They come up with several different ideas to try and get Darren back including 'cheating' photographs and breaking and entering. All of these plans are foiled but there is one plan that they hope will work. In high school Darren was in love with another girl, Sandy Perkus (Amanda Detmer) and she is back in town so the two guys try to persuade her and Darren to get back together.
Then they kidnap Judith and tell Darren she is dead so that he will get back together with Sandy and they can all be friends again. But Judith knows it is Wayne and J. D that have kidnapped her so she eventually figures out a way to get out and when she does she sees that Sandy and Darren are back together but Darren had promised Judith they would get married so they still carry on with the wedding after Sandy runs away to finish becoming a nun. Wayne and J.
D are put in jail for kidnapping but are then broken out by their former gym teacher, they then go and stop Sandy from becoming a nun and tell her Darren still loves her, then they kidnap Neil Diamond in the assumption that he will help get them back together and then they go to the wedding. Neil Diamond plays for them and Darren realises the error of his ways and goes back to Sandy. Judith, heartbroken, then turns and goes with Wayne, and J. D and the coach admit that they are gay and they go together.
On stage that night Neil Diamond weds Darren and Sandy, Wayne and Judith, and J. D and the coach. The film ends on a humourosly happy ending..