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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. She tells him to take a two-month vow of celibacy, break off his relationship with his current girlfriend, and revisit some of his ex-girlfriends to help him figure out where he went wrong in his past relationships. Sue Carlson, his first serious girlfriend, tells him he has commitment issues and is always looking for "the next best thing". Erin Moran, his "Happy Days" co-star and the girl he lost his virginity to, tells him he needs to face his fear of other people by joining her at an autograph signing.

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 on. Julie gets her revenge by publicly humiliating Scott as part of her stand-up comedy routine. Scott's friends then whisk him off to Palm Springs, where Scott encounters a wild bachelorette party and gets some unexpected advice from an elderly couple who are still in love -- and still sexually active.

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 looks. Meanwhile, Scott's friends try to derail his quest to remain celibate by sending a stripper to his house. When Scott finally meets his so-called "perfect match" on a blind date, he learns that his natural instinct is to take even the perfect woman and nit-pick her to shreds.

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. Doc Ali grants Scott a temporary furlough to see Renee, but she also assigns Scott to spend some time in a day care facility with other people's children. After spending the day wiping noses and cleaning up messes, Scott finds out that taking care of a 17-year-old can be just as hard as dealing with a room full of 3-year-olds.

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 Connie, then sends Scott with his friends to a cuddle party, where Scott learns from spooning with strangers that there is more to intimacy that just sex.

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 for a serious relationship and orders him to break off his friendship with Johnny. Meanwhile, Scott's friend Cuccio asks Scott to be the best man at his wedding. This leads to Scott planning a bachelor party for Cuccio, including a visit from the Morrell Twins, two Playboy Playmates that Scott and Cuccio dated together. Johnny's antics at the bachelor party upset Scott so much that he finally gets the nerve up to put his friendship with Johnny on hiatus.

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. Scott weighs his decision as he helps his friend Cuccio prepare for his own wedding -- shopping for the ring and talking to an attorney about a pre-nup. Scott's friends then throw him a graduation party to celebrate the end of his therapy, where Scott tells Renee his decision: can he or can't he commit to her. Renee in turn gives Scott some very unexpected news! Stay tuned to find out what happens.