Charlie discovers that being a children's singer means making lots of money and picking up single moms. But he also discovers that he's going to have to overcome his fear of performing in front of large audiences.
Charlie is acting even more promiscuous than normal, which is getting him in trouble with a lot of husbands and boyfriends. With the help of his psychiatrist, he discovers it's related to his ex-fiancée's upcoming wedding.
Charlie dates a self-help author who is much older than he is, has a 32-year-old son, and treats Charlie more like a son than a boyfriend. Jake tries to write a book report over the weekend, but keeps losing the book before he can read it.