Three best friends form a Neil Diamond tribute band called Diamonds in the Rough. They have been best friends since elementary school and have been Neil Diamond fans just as long. After a gig at a local bar Darren Silverman meets a beautiful psychologist named Judith. Six weeks after they start a relationship, Judith is still only allowing Darren to watch her undress and change clothing. She insists that he quit the band and completely cuts him off from his friends. She forces him to go through embarrassing medical procedures and couples therapy, all of this for nothing more than a sore mouth from make out sessions at night.
Wayne and J.D., Darren's two best friends, form numerous plans to save him from her cold cruel clutches. They try to bribe her. They try to arm wrestle her for his freedom. They even go as far as to make fake photographs of Darren cheating on her. Nothing seems to work to bring back their friend.
When Darren and Judith announce to J.D. and Wayne that they are engaged, they decide to kidnap Judith. After the kidnapping they seek out the advice of an old coach currently serving time in jail. His advice is to kill Judith, but instead they lock her in a basement. Then J.D. and Wayne try to set up Darren with Sandy, an old love interest, who happens to be about to become a nun.
On their first date Darren is so distracted with the disappearance of his fiancé that Sandy is heart-broken and returns to the convent. Darren quickly realizes his feelings for Sandy and runs a full 30 miles all the way to her convent to win her heart back.
Judith escapes the basement where she is being locked up by Wayne and J.D. only to find Sandy and Darren kissing. She forces him to explain to Sandy that they are engaged. Sandy again returns to the convent heartbroken, and both Wayne and J.D. are arrested. However, they escape with the help of the coach and take Sandy to break up Darren's wedding.
They arrive at the wedding with Neil Diamond, Sandy, and the Coach to break up the wedding. Judith and Wayne start beating each other up and realize they have feelings for each other. In the end there is a three-way wedding, and everyone is happy again.