Charlie tries to set up Alan with the sexy and rich new next-door neighbor who is looking to settle down. But when Charlie discovers her secret history as a drunken slut, he decides to go after her himself.
After Charlie and Alan tell their mom that nobody loves her enough to attend her funeral, she replaces them with a new family, which makes both of them very jealous.
Alan thinks he's making his last alimony payment to Judith, but Judith's future sister-in-law could be putting the wedding in jeopardy. And things only get worse when she hooks up with Charlie.
Everyone suspects that Alan may be coming out of the closet when he becomes good friends with a gay man. But Charlie is actually the one who is suddenly feeling insecure about his sexuality.
When Alan has to go renew his driver's license, he convinces Charlie to help Jake with book report. But when Charlie takes Jake to the track, instead, Jake's horse comes in.
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 and 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.