After Mary unexpectedly un-invites her family to watch her play basketball at an important game, the Camdens begin to make other plans for themselves. Lucy is angry with Mary because she invited Ashley--a popular girl in Lucy's school, to her game. Simon, Ruthie, and Happy get lost in town while pretending to be spies and following their mailman all over town. Lucy was supposed to to be babysitting them, but was instead entertaining herself and Ashley by talking on the phone with her boyfriend Jimmy Moon. Eric is faced with counseling a young boy who is once again back on his drug habit that is affecting his family.

Simon rightly fears he'll catch roommate Ruthie's chicken-pox, but his enterprising hygienic measures fail to prevent contagion from her, or from Happy's fleas. When a robber carjacks them, Annie seems calm and hands their valuables, so Matt feels 'unmanly' and guilty. However, Anne breaks down at an identification lineup. Jimmy Moon stands against Lucy in the school elections, then turns to her parents for help. The church organist veers bizarrely from brilliance to disharmony.

Mary tries to impress her basketball team by stealing a glass from their teen hangout "The Varsity", which is a school ritual. A misunderstanding occurs which winds up with Matt being arrested for stealing the glass. Lucy cheats on a school paper by taking one of Mary's old papers and putting her name on it. Ruthie asks Simon about help when she overhears her father talking about how it bothers him when people in America don't know the National Anthem.

The school bully experiences a severe lapse in judgment when he tries to sexually harass Mary.

After a failed table-spread trick before the arrival of his new magic kit, the 'Great Simoni' can't convince Ruthie to act as his assistant because she'd rather wear the cape even without aspiring to become a magician; Lucy's grades slip as she starts hanging out with 'the laid-back crowd'; Eric's church is in the running for weekly local TV broadcasts if next Sunday's liturgy goes well, and he obsesses over writing the perfect sermon; Mary considers quitting basketball when Coach Koper is focused on a new star player; while Annie spends a long day running errands, Matt bows out of keeping order at home. After Ruthie answers a phone call from the Colonel and tells him what's going on, he turns up unexpectedly to 'assume domestic command.'

Even bright teacher's pet Simon is terrified by new bully science teacher Hunter to the point of faking illness to avoid a private meeting with her about his solar system model, which actually is part of a superb presentation. Softie Matt already turned down dates to the party after Mary's return to the basketball team, yet she complains to everyone, even hunky jock ex Richard, who ends up making her day.

Simon's classmate Mark Huff's father Carl is stopped by a light push from caring biology teacher Lane to storm at his boy. When Carl complains to the principal, Simon dares only say he didn't get a clear view, then feels morally guilty for not having prevented a fine teacher being suspended, later even dismissed. Eric finds out Carl is a domestic bully and gets Lane reinstated. Matt and his friend Scott misread apparently sexual signals from a teaching assistant, which causes repeated havoc for Matt. Rather then let Annie chose a disastrous 'pregnancy project', Eric arranges a handsome piano teacher, Josh, who flirtatiously restores her self-esteem.

After drinking Matt's coffee once, Simon fears to be addicted and acts accordingly. A natural, legal 'supplement' is offered to study-exhausted Matt by buddy Scott, whose father got it in a health store, and to Mary by over-competitive teammate Diane Butler, whose father uses it himself. Eric realizes it contains dangerous ephedrine. Eric's former rock band mates visit GlenOak. Matt sets something right. The Butlers are in for a shock as Diane suffers a fatal heart attack from the ephedrine.

A school janitor claims that God is talking to him. So the school wants him to retire with his pension intact but if he continues to act the way he does, they're ready to dismiss him which means he'll lose his pension. So Eric tries to talk to him but he steadfastly maintains that God is talking to him and that he has a mission.

Matt tutors silver spoon James Potter in history, refuses to help him cheat but is still in trouble when the professor smells a rat. Simon's new classmate Lee Patterson boasts his cool dad works with FBI and even NASA, but actually is an unemployed ex-con and petty marijuana dealer. Lucy regrets taking a school secretary job, is flattered when older hunk Tyler asks her for a dance, but that bubble bursts when he actually wants the password to enter the school computer.

Simon is in absurd trouble just because his mother and the principal make a huge drama of a finger-gesture among schoolboys. Matt tries to explain, but Simon feels he's robbed of another part of his childish innocence. Matt wrestles with domestic problems among his roommates and considers moving back home on account of Eric's cardiac condition. Basketball coach Jason Cleary decides the girls' continuing grades slip warrants drastic action: a team lockout, which makes the local TV news and because of official secrecy starts a rumors circuit.

The whole community is shocked to see Mary and half her Wildcats team meanly vandalized the school's gym. Simon and Ruthie feel guilty for not telling they overheard her planning 'something extreme', so they seek redemption in Catholic confession, a synagogue and a Buddhist temple. Matt feels guilty enough to move back in and resume his task as big brother, only to find that o longer requires his presence and return to his house-mates. Eric calls a marker on lawyer Bill Mays, he gets her in to a trial-avoiding parole office 'last chance' program.

Simon and Lucy talk about their parents lives. When Eric and Annie overhear them, they are hurt by the discussion. Mary has dreams of being a basketball star and a talent scout contacts her.

The next Valentine's day, Robbie prepared a surprise for Joy. Mary meanly supposes the hotel she overheard him contacting by phone means another sex trap. Joy, who assumed the butler to be away like her father really is, isn't discouraged, but bitterly claims Robbie doesn't love her truly because he refuses to risk getting intimate. Matt contacts all his 'true lovers', wondering why he never stayed hooked up. Lucy again assumes Jeremy, who is back in town and double-dating with Mike, wants her back and pretends to have a date. Mary is shocked to see Wilson moved back and goes steady with her former school friend Corey Conway. Simon gets permission to let his hot senior date Maria 'help babysit' and gets her cute kid brother Jake to spare Ruthie dateless embarrassment.