Simon is surprisingly successful with Eric's suggestion to show how mind-games can convince people of crazy ideas by pretending he's shrinking; when he's overheard, Matt turns the tables, only to be beaten in the end. Lucy invites her classmate Shelby to dinner, curious about rumors that she suffers from bulimia; Eric lets Mrs. Bing drag him into meddling in her friend Mrs. Hinkle's situation.

Because Mary is desperate for a date with Matt's classmate Brian, who isn't interested in her, Matt pays him $20 to take her out for pizza. They have a good time--until Mary finds out about the plan. Meanwhile, Simon uses his own coaching method to teach Ruthie swimming in the bathtub to save her from embarrassing baby-class swimming lessons; and Eric finds that he can't fit into his jeans anymore, but when jogging only makes him hungry, he pays Matt to sneak in junk food.

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.

The whole Camden family is invited to Matt's deaf ex Heather's wedding to Mason, celebrated by Eric. Matt brings current girlfriend Shana, yet ends up convincing the bride to leave the groom at the altar and drive away together. Wile his ex Lucy flirts with Joe, Jordan gathers the courage to tell her he's dating Mary. Simon is confused after being kissed by Deenah's cahoot.

Matt brings unamused Heather, who hoped he would propose again, back to church, where he exposes after some hesitation groom Mason's flaw, while desperately trying not to lose 'abandoned' Shana. Simon learns the kiss was a 'love test', which is rewarded with more, and Jordan encourages to just enjoy it without excessive worries. Jordan tells Lucy, who out of mere jealousy makes out with wedding guest Joe. Eric has a hard time accepting Julie's sudden announcement to marry Dr. Hank Hastings, but doubts soon shake that couple to be.

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.