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- In 1950s Brooklyn, 14-year old Alan Silver prepares to go to his first dance with a girl and has a falling out with his best friend Benny Belinsky.
- Alex's friend dies in an accident. As the family grieves, Alex tries to mask his pain, but he can't hide his sadness and other emotions forever.
- When Sheridan goes public about the Winston administration's links to organized crime, Mike decides to take the fall and save everyone else. He submits his resignation, leading everyone to drown their sorrows and say their goodbyes.
- After getting a high score on an entrance exam, Alan is accepted to a prestigious high school. While Phyllis is excited about the news, Alan and others have reservations about going to a new school.
- When Cousin Jacob arrives in Brooklyn from the old country, Sophie goes to great lengths to cover up Jacob's tragic past from the kids.
- Sophie and Jules become really worried after Aunt Sylvia takes Alan on a trip into Manhattan to see the famous writer Jack Kerouac.
- In 1956, 14-year-old Alan Silver's life revolves around family, the synagogue and the Dodgers. Grandparents Jules and Sophie live in the same brownstone as Alan, his brother Nate, and their parents Phyllis and George.
- When Katie's family objects to him taking Katie to a couples only party, Alan comes up with a plan where he asks Benny's dream girl to the party, has Benny escort Katie and then they switch dates at the party.
- Katie's sister announces that she has eloped, gotten pregnant and will be moving to California. Everyone is happy for her except for her father, who refuses to attend the going away party.
- When Brian and Kate confront him about his poor grades, The Brady Bunch (1969) addict Ross says that he wishes that he were living with the fictional Bradys. He gets his wish.
- Alex starts his sophomore year looking for a girlfriend in the freshman directory. He meets Tricia, who seems to be everything he wants. However, after a spat with Tricia's roommate Ellen, Alex finds that despite having nothing in common with Ellen, he is developing feelings for her.
- Alex is an emotional wreck, still with boring Tricia - who he doesn't care for - after kissing her intriguing roommate Ellen, who turned back to accept her Dennis' proposal to a sudden wedding in Pennsylvania without a single guest. Alex even worries so much that the whole time allotted for a Leland test essay he would have aced elapses without him writing a single line. After Ellen agrees to Alex's offer of a ride to the train station, he is filled with hopes of stopping her, but is once more unable to express his emotions. Once Alex has gathered the courage at home, he drives all the way to race her train to its destination, but arrives just minutes after it has come and gone - so it appears to be too late.
- A friendly poker game involving Jules and Myron reignites an old feud.
- After Sophie accidentally breaks Sid's store window, they disagree on a damage estimate, prompting Sid to take legal action.
- After Katie's father refuses to let her continue seeing Alan due to their religious differences, Alan and his family setup a dinner appointment with her family in the hope of breaking the ice.
- 1996–200230mTV-148.5 (208)TV EpisodeMike's political mentor comes to City Hall to help on the Millennium project, and displays a literal Messianic complex. Things heat up between Randall and Janelle. A mishap occurs when Paul dog-sits Rags as a favor to Carter.
- Mallory introduces her new boyfriend, Nick, to the family. He isn't well received, and Steven realizes that he needs to trust Mallory and let her make her own choices.
- When Alan makes it know that he does not want to attend the Bronx School of Science, his parents begin to argue about whether he is making the right decision.
- Following a fight with Alan, Benny temporarily goes missing. When the dust is settled, Alan must come clean to Karen while Katie is forced to come clean with Benny.
- On his first day of high school, Alan is the envy of his friends when an attractive girl with a reputation asks him to tutor her in science.
- The family gets alarmed when Alan begins hanging out with a group of older rebels from school who are a bad influence.
- On a Saturday, the guys, who are supposed to be clothes shopping, sneak off to Coney Island. Meanwhile the women who are supposed be at the laundromat, sneak out to a Danny Kaye movie.
- When his favorite teacher announces that she is leaving, Nathaniel does not want to accept the new teacher and begins to act out in school.
- The parents are away for a few days, Alex is in charge but cares only for his date Monica, so he wants the girls out; Mallory 'drives' straight into a telephone pole, now they must come up with some $300 to pay for repairs. Alex decides to earn enough by renting out rooms with ocean views to traveling Leland sports game attendants, who certainly bid enough to make a profit on top. Skippy, who can't go home, is happy to stay as unpaid bellhop and sleeps on the floor like the girls, 'hotel manager' Alex gets the couch and can't resist to keep the sweet money flowing in. Then dad calls: he'll be home in a few hours. The guests even brought fellow Leland fans to celebrate their victory frat-style...
- As Alex packs his belongings for a move to New York, each family member has a chance to say goodbye. Nick and Skippy show up to help Alex pack, and his ex-girlfriend Lauren brings a gift.
- Alex turns to amphetamines to get through a particularly stressful period of exams and scholarship applications.
- When a distant relative dies, Alan worries that the funeral will interfere with him taking Katie to a Brooklyn Dodgers game.
- Aunt Sylvia comes over for dinner and makes a surprising announcement which divides the family.
- After Alan's "switching dates" plan backfires, Benny decides that they can no longer be friends since they are competing for the same woman; Aunt Sylvia starts up a post-divorce relationship with Sid.
- Alan wins a chance to compete on the television show "Happy Felton's Knothole Gang" at Ebbets Field.
- Muckraking reporter Wayne Sheridan wants to connect Randall's administration to organized crime. Several staffers make this easy, including Randall and Nikki. Randall gives a sanitation contract to a mobster, whom Nikki is dating.
- Paul's leg injury, Mike's toothache, and possibly falsified resumes all get mixed up with accidental insults to the hearing-impaired community.
- Randall hosts a New Year's party, where Nikki's boyfriend dumps her for the catering girl, Carter helps Stuart grieve over a deceased house pet, everyone suggests resolutions for each other, and several people drink way too much alcohol.
- A rainy day prevents the guys from seeing the Statue of Liberty, so instead they play indoor games. Bernie introduces his new fiancee to the family.
- After jogging with Elyse, Steven feels chest pains. He is taken to the hospital, and they find out he had a heart attack. While there, the family meets relatives of patients who suffered heart attacks, while facing the issue of mortality.
- Steven has an operation to clear a valve after his heart attack. As they wait and worry, Elyse and the kids remember life with Steven. They take comfort talking and sharing with other people, while their concerns over the future deepen.
- Family and friends continue their vigil while Steven has his operation. The operation is a success, and home they go. But Steven has to adjust to restrictions in food and activity, while the family treats him as an elderly invalid.
- Mallory and Nick are determined to get married, so they decide to elope. Alex tries to talk her out of it, but only after they have been gone for some time does he go after them. When Steven and Elyse learn of this, they panic; Steven hopes Alex can stop them, while Elyse concedes they'll have to grudgingly accept the situation. But while waiting for the justice of the peace to be available, Nick has second thoughts about what they're doing.
- Jennifer's actions instigate a meeting of the school board to discuss if "The Adventures of Huckleberry Finn" or other books should be banned from being read by students.
- Andy becomes the official school buddy for a new boy in his kindergarten class. Josh is deaf, and he and Andy become good friends. When some other kids pick on Josh, Andy stops talking to become closer with Josh.
- Teacher/parent interviews at Alex and Mallory's school become interesting when both Steven and Elyse contend with a rude, insufferable teacher.
- 1996–200230mTV-148.0 (130)TV EpisodeStuart breaks up with Deidre, who files sexual harassment charges against him. Stacy's visiting aunt Marie hits on James. Randall starts a romance with a staff member.
- Nikki breaks up with Arthur and joins Mike for a hotel tryst, which goes awry when Mike wants to keep their relationship secret. Stacey plays a phone prank on Paul. Carter, James, and Stuart all go on a stakeout with Randall.
- Paul and Claudia's wedding day is fraught with problems: Randall suddenly suffers from a speech impediment and best man Mike learns that the church is double-booked with a funeral.
- With his family out of town, Alan along with Warren and Ben invite Katie and her friends over for a dinner party.
- Nick is worried that the constant disapproval he receives from Elyse and Steven will ultimately cost him his relationship with Mallory. Eager to change, Nick turns to Alex for help. Unfortunately, Nick turns into another "Alex," and while he is now pleasing to Elyse and Steven, he turns off Mallory.
- Alex hires a 13-year-old tutor, Eugene Forbes, to help him bring his grade up in advanced geometry from an 89% to 90%. However, Eugene is immediately distracted when he meets Jennifer, and he struggles to learn how to take a break from being an intellectual genius and to be a 13-year-old kid. Meanwhile, Steven is struggling to keep the family's spending in check.