Sarah's father brings drunk driving charges against Bailey. Owen has a new-found fascination with women's clothing and Charlie stresses about it. Julia has trouble adjusting to married life with Griffin. Claudia tries to become "popular" in high school. She auditions for cheerleading, ends up as the school mascot (a possum), and meets a cute guy.

Bailey decides to plead guilty to the charges in order to keep Sarah from having to lie to the court and to keep his family from getting a second mortgage on the house to pay for his lawyer. He is sentenced to probation and community service, and loses his driver's license. Charlie decides to withdraw Owen from pre-school when a rumor about his teacher Jenny abusing children starts to circulate. Griffin has a friend come to stay with him and Julia who makes the newlyweds examine how their married lives are going to work. Claudia snoops in Reed's locker and gets busted, but Reed realizes that Claudia is only interested in him, not malicious. Sarah ends up packing a bag and leaving with home, unable to deal with her parents anymore.

Bailey can't get a job (and therefore an apartment) because of his criminal record, and Sarah loses her money to a dishonest landlord, so they solve their problems together by taking on a job as building managers and sharing the free apartment that comes along with the job. Claudia is horrified that Bailey will be speaking at what is now her high school, and feigns sick. Charlie, with some prodding from Claudia, goes out on a number of disastrous dates. Griffin doesn't tell Julia about his financial problems and she buys new clothes for work. Charlie realizes that he's been giving Julia a hard time lately partly because he misses her around the house and partly because he's jealous of the love she has with Griffin.

Owen finds Charlie the perfect woman in the grocery store, but Charlie keeps getting mysteriously sick every time he goes out on a date with her. Claudia practically knocks herself out to please Reed. Julia gets in hot water at work when a co-worker thinks she's sending mixed signals and kisses her, only to find out she's married. Bailey and Sarah plot against the woman in apartment 14 who complains rudely all the time about the service in the apartment building, until Bailey finds her at an AA meeting.

Bailey and Annie begin to bond over their mutual addictions, and when Annie finds out that Bailey and Sarah aren't a couple, she decides to make the first move. Julia's on-the-job troubles start to get worse, as Griffin finally comes to the realization that something is wrong. Just as Charlie and Nina's relationship begins to progress, the two begin to argue over different philosophies of life. Nina, the bird researcher, finally makes Charlie see that nothing will be possible for himself until he learns to be more accepting.

Griffin feels like Charlie hates him, and follows Julia's advice to try to get to know her brother better. Claudia pines after the oblivious Reed who asks a different younger girl out on a date. Charlie sees Kirsten again and finally gains some closure from his relationship with her. Charlie tells Nina he loves her. Bailey and Annie start to pursue their new relationship, but call it quits when Bailey's sponsor disapproves.

When Charlie collapses on the racquetball court, he confides in Kirsten, but tells no one what happened. Not wanting to tell Julia the extent of his financial problems, Griffin is forced to borrow a large sum of money from a business associate. Sarah decides it is time to lose her virginity, but isn't able to go through with her decision. Bailey, shocked by Sarah's decision, falls into bed with Annie.

Charlie tells Nina that he's sick, and although she tries to put on a brave face, he realizes that she can't handle the news. Just before they renew their vows, Julia finds out about the financial troubles that Griffin has been hiding. Bailey makes a last minute decision to bring Annie, and therefore Natalie, to the wedding, and Natalie causes disaster after disaster.

Charlie's plan to tell each family member the secret he's been hiding backfires as each person struggles to deal with the facts. Meanwhile, Griffin and Julia begin to deal with their financial problems.

Charlie begins his radiation regimen and soon experiences its accompanying unpleasant side effects, but has trouble accepting the help his family is offering. Julia gets a wake up call from Sarah and finally realizes that she has to get a real job, one that she hates but that will earn her much-needed cash. Bailey, unable to do anything for Charlie, misdirects his frustration towards Annie, who blows up at him. Claudia is furious with Julia and Griffin because they decide to save money by firing Reed from his part time job at the bike shop.