In order to figure out why he has been unlucky in love for the past 45 years, Scott Baio hires a life coach named Doc Ali who will help him figure out where he went wrong with his past relationships.
Scott confesses to Doc Ali that he has had trouble staying faithful in relationships, so she sends him to visit Playboy Playmate Julie McCullough, an ex of Scott's whom he relentlessly cheated...
Doc Ali confronts Scott about his tendency to only date busty blonde bombshells, then sends him off to a matchmaker service to help him find a woman he would be compatible with, regardless of her...
Scott receives word from his girlfriend, Renee, that her 17-year-old daughter is going to be in town and that she would like Scott to meet her.
After telling Scott that he has never been able to have emotional intimacy with a woman, Doc Ali orders Scott to break off a long-term "friends with benefits" relationship with his friend...
Doc Ali asks Scott for the opportunity to meet his friends, in order to see how they influence him. She discovers that Scott's friend Johnny is a detriment to his ability to prepare himself...
In the final week of Scott's therapy, Doc Ali asks him whether he is truly ready to make a commitment to his girlfriend, Renee.