Jake is ready to begin junior high school, until Alan scares him by telling him about all of the horrors that he experienced. Meanwhile, Charlie has a rash in a most inopportune area.
Charlie and his mom temporarily become friends until Charlie takes an interest in one of her married clients; Alan goes to bed with a woman who has self-esteem issues.
Charlie humors Alan by going on a date with a woman his own age instead of a young bimbo. But when the woman rejects him after the first date, he becomes obsessed with seeing her again.
Charlie hasn't had a paying gig for months, so Alan becomes part of a drug study to make extra money. Meanwhile, Charlie tries to bond with Linda's four-year-old son.
A medication mix-up causes Charlie to humiliate Linda at an important dinner, and Jake disobeys his dad's orders and sneaks out to attend a rock concert.
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 ignores his future step-father's advice and gets involved with his daughter, and he learns the hard way that he should have heeded the warning.
Alan sleeps with a woman he and Judith were friends with when they were married, who then tells him that Judith says her new husband is a better lover than him.
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.
Alan has a crush on Charlie's new older girlfriend and Charlie discovers that he "dated" his girlfriend's son's fiancée. Meanwhile, Alan tries to get Jake to study for his algebra exam.
