Here We Go Again
Eric opposes Annie's decision to go back to school, while Annie thinks he's making her bear the brunt of his anger at Mary's decision to skip college. Meanwhile, Heather and Matt's on-again-off-again relationship threatens to be off again permanently; Mary decides to buy a car; Simon gets stressed over his first day of high school; and Lucy is ready to begin a relationship with Andrew Nayloss, except he hasn't come back from summer vacation yet.
Help
When Mary loses her job at the pool hall, she becomes desperate to find a way to pay her mounting unpaid bills. The Colonel pays an visit to the Camden house and surprises Annie and Eric . Matt blames everyone but himself for failing organic chemistry, Lucy asks Simon to help her win homecoming queen and he gains popularity in the process. Ruthie's quest to be transferred out of her teacher's class is granted when she qualifies to enter a private school.
Losers
Eric and Annie decide to enjoy a Friday night out separately. Eric hangs out at the pool hall and Annie has dinner with her college professor. Meanwhile, Lucy stays at home to babysit the twins, Ruthie and her homework assignment: an egg that is supposed to teach her about the responsibilities of parenting. Simon is left waiting at home when Matt forgets his promise to drive him on a big date with a sophomore girl. Mary starts another minimum wage job at a pizza parlor and makes some unlikely friends.
Busted
Exasperation reaches an all-time high in the Camden household, as Eric and Annie helplessly watch their oldest daughter Mary and her worrisome friends continue to head down the path of destruction and into the hands of the law. When Frankie expresses interest in signing up for college classes, Mary starts checking out Lucy's early application packets. Meanwhile, Simon has a hot date, Lucy gets a weird proposition from a classmate, and Ruthie discovers manipulative fun of keeping a diary --- much to the embarrassment of Eric and Annie when she sees them having sex !
Blind
Desperate for some cash, Mary agrees to babysit for her young niece. When she agrees to also watch her friend's baby, Mary discovers a bottle of beer in the diaper bag. When her aunt and uncle return home they find the babies alone, the empty beer bottle on the coffee table and Mary no where in sight. Disappointed, they ask Mary to leave and discuss whether to tell Eric and Annie about her further decline. While having lunch at the pool hall, Eric and Annie see Mary's friends fighting. Trying to step in at the right moment, Eric breaks up the two and gets a black eye in the process. Back at the Camden house, Lucy takes on the responsibility of Ruthie's sleepover and taking care of the twins as Simon decides to get his ear pierced without his parent's permission.
Broke
Mounting unpaid bills loom over Mary as Eric and Annie discover the trail of lies and manipulation that she has left behind. The Camdens fight over how to handle her behavior and the disruption affects the entire household. Lucy and Simon battle a persistent credit card collection agency who thinks Mary is avoiding their phone calls. They then enlist Matt to help them devise a plan to help their sister pay her bills. After his weak attempt of pretending to be Mary's lawyer "Bernie," Ruthie suggests they borrow the twins' piggy bank savings to temporarily help Mary. Meanwhile, Mary takes her last $20 and goes to a double-feature movie and buys some ice cream.
Bye
Eric and Annie call family and friends to find out where Mary got the money to pay her bills. Their investigating leads them back to their own home. Each of the Camden kids at first deny helping Mary. However, Ruthie gets caught trying to fill Sam and David's piggy banks with rice so it doesn't feel empty. Matt , Lucy , Simon and Ruthie confess to borrowing the twins savings so Mary could pay her debt. The seriousness of the situation force Eric and Annie to take immediate action. The family gathers to confront Mary with their hurt feelings and the decision to send her to live in Buffalo with the Colonel and Grandma Ruth.
Gossip
The Camdens face ugly rumors, about Mary's leaving home, from church membres and the community. Simon uses his new-found cool status to date identical twin "bad girls" Carol and Sue Murphy (guest stars Mary Kate and Ashley Olsen, "Full House"). Trying to impress the girls on a date, they shoplift, skip out on a restaurant bill and sneak into the movies, but their behavior and the cops catch up with them. Meanwhile, Lucy breaks her date for the school dance because she's concerned about her friends gossiping about her and who she's going with. She realizes that it doesn't matter what anyone thinks and takes Ruthie and the twins to the dance to meet her date and apologize.
Tunes
In an effort to fit in at school, Simon starts hanging out with a rebellious, misogynistic group of kids who listen to explicit rap music. After one of these friends harasses Lucy and Annie , both Eric and Annie confront Simon about his behavior and demand an apologize from his friends. While Simon waits to talk his friend at Matt's place, his friends attack Heather on the street. Simon and Matt run out to rescue her as the police arrive on the scene. Later on, Simon apologizes to Annie for his lack of judgment.
Surprise
Despite the disapproval from the rest of the family and his own hesitations, Eric takes in Mary's ex-boyfriend Robbie Palmer to live with the Camden's for the night after learning that he's homeless. Matt also shows up unexpectedly after being kicked out of his apartment by John, who needs quality time with his girlfriend. Meanwhile, Mary calls home again and hears Robbie's voice on the other end and assumes he's dating Lucy now. Also, John proposes to his girlfriend Priscilla in front of Matt.
Home
A month has passed since Eric invited Mary's ex-boyfriend to stay with the Camden's until he got on his feet. Robbie happily continues to act as a member of the household--- and it's driving Annie crazy. Robbie is Eric's latest 'project', Ruthie's new best friend, recipient of Simon's financial advice, and according to Mary, Lucy's boyfriend. He's even cooking and folding laundry. Frustrated and emotionally strained, Annie starts to think nobody needs a mother anymore. Also, Matt also feels unneeded from the family due to Robbie and pays an unexpected visit to Heather and her new boyfriend.
One Hundred
Eric becomes convinced Mary has run away from the Colonel's to come back home. He goes through great lengths to find out if it's true. In reality, Mary is coming to surprise Eric for his birthday. The Colonel and his household help Mary keep her surprise. Meanwhile, the rest of the Camdens act strangely around Eric as they all work on their surprise party for him. Eric discovers when Mary's flight is getting in and meets her at the airport where she tells him she is only staying for an hour to tell him she loves him. When Eric returns home, Annie has filled the house of all the people in the community that Eric has helped. As an extra surprise, Lucy tells Eric she's decided to become a minister.
Kiss
After their lackluster attempt at kissing, Mike and Lucy agree to be friends and to fix each other up on dates--- but the plan bothers Lucy more than she anticipated. Meanwhile, Matt's in a huff over John and Robbie's newfound friendship and feels slighted by the family. Eric also continues to feel alienated from his family when they keep going to Annie for advice. Also, Annie feels slighted when Ruthie plays an un-funny joke when the twins recognize her as their "mama".
V-Day
Mary discovers Robbie has a secret date for Valentine's Day. She enlists the whole family to help her uncover who the mystery woman is. Lucy has a dreamy first date with Jeremy , but the rest of the Camdens suffer from failed plans. The remaining family end up celebrating Sam and David's second birthday.
Sweeps
Mary convinces Eric and Annie that she is ready to come for a visit, but the whole house is apprehensive about her intentions, especially Robbie, who quickly learns Mary's real reason for coming home. The attention is averted, however, to the boys in the house when a condom is found.
Parents
Robbie's dead-beat dad shows up unexpectedly at the Camden household and convinces Robbie to move out with him against Eric's wishes. Meanwhile, Ruthie turns to Mary for advice on how to get around their parents' rules, and Annie worries when Lucy starts spending a lot of her time with her friend's "unmotherlike" mom.
Crazy
Matt begins to go crazy over a psychological evaluation that he is required to take for his medical-school application. Matt also notices the strange demeanor of his psychologist, which leads to a surprising twist. Meanwhile, after Ruthie gets into trouble at school for missing homeroom classes daily, she tricks Robbie into coming to talk to her principal. Simon decides he no longer wants to be together with Sasha since they have nothing in common and that she is not that intelligent, but the plan backfires on Simon. Also, Mike wants to try to be in a relationship with Lucy again, but unfortunately she turns him down since they are both on the rebound from Jeremy and Elaine. Lastly, Eric must convince a terminally ill patient to embrace life no matter what the doctors tell him.
Apologize
Robbie meets a girl named Marie who is a striking resemblance of Mary. Annie invites Marie to stay for dinner. Robbie tells Mary about meeting her look-a-like and she takes the news badly. In the meantime, Mary doesn't tell Robbie that she ran into Wilson in Buffalo and was planning on going to his place for dinner. Robbie finds out about it from the rest of the Camdens and confronts Mary about it. Matt meets Robbie's ex-girlfriend, Cheryl, at a restaurant where she works and asks her for a date.
Virgin
Annie discovers a flirtatious mother of one of Lucy friends, Serena, is seeing Eric for therapy sessions, and requests that he refer her to someone else. Annie then has to deal with the guilt over her jealousy-induced interference. Simon is mortified when word gets around school that he's a virgin because Annie told Serena about his lack of sexual experience. And, Matt procrastinates telling Robbie that he is dating Cheryl.
Regrets
Annie receives the shocking news from her father that she has a step-sister. Annie takes the news hard but Eric convinces her to make the effort to get to know the woman, Lilly, for the sake of her ailing father. Meanwhile, Ruthie protests the unjust firing of one of her teachers, speculating that racial discrimination may be involved. The entire community makes a big fuss about a petition protesting the apparently unfair firing of a teacher at Ruthie's school. Matt, however, knows the real reason why she is leaving, which could be rather embarrassing for the petitioners. The teacher has advanced breast cancer and didn't want to alarm her students, so she let everyone believe she'd been fired.
Chances
Not even the Camdens are immune to love's pitfalls as their relationships hit a few new bumps. Mary is back in Glen Oaks for the summer, but fears about being together again have Robbie a bit on edge. Meanwhile, Eric and Annie are the recipients of what may or may not be advances from unmarried acquaintances. Matt agonizes over telling his family about his relationship with Cheryl. John and Priscilla move their wedding to New York so John's ill grandmother can be with them. Simon tells Deena they can not be friends because he wants to be her boyfriend. And, Lucy surprises even herself when she proposes to Jeremy. Eric and Annie give Lucy and Jeremy their blessing on the engagement.
Are
Mary tries to explain to Lucy that nothing impure happened between her and Jeremy. But Lucy is still skeptical. James tells Eric he tried to have an affair with Annie. Eric counsels him that he will find love again if he could love Annie. Serena also comes clean with Annie about her attempted affair with Eric. Mary tells Robbie he will always be a part of the Camden family regardless of whether or not they are dating. Eric and Annie give their blessing to Lucy and Jeremy's engagement. Simon tells Deena they cannot be friends because he wants to be her boyfriend. Matt decides to pursue a relationship with Cheryl on a "date-by-date" basis. Wilson asked Mary to go back to New York with him for the summer. And John and Priscilla move their wedding to New York so John's ill grandmother can be with them.
