Mona moves to New York to her brother and Tony gets her apartment so he can live up his bachelor's life. But after the opening party the normal life returns and Tony misses his old environment.

Mona's brother has bought a seedy hotel in New York and used Mona's money for it, too. Because the hotel means a lot for him, Mona goes to New York to help him shape it up again.

Tony has met Fiona at the dentist and get her a job as secretary at Angela's agency. The tidy-minded perfectionist Fiona is Angela's dream but also Mona's nightmare. After an argument between Mona and Angela Fiona quits because she doesn't want to stand in the way of the both. But Mona quits, too.

Sam wants to queue for cards for the Beastie Boys concert overnight. Tony allows it not without remarking he has done much wilder things in his youth. During the stories told by Tony and Mona, Angela realizes that she has missed a lot. Now she wants to catch up on some 'action'. So she makes up a list what to to: Among these is a meeting with Jake 'The Snake' and a trip to his 'Rock of Inspiration'.

Through Tony's new girlfriend Casey Angela's got a new commercial order for Armando-Fashionwear. But she couldn't think of any spot. Age, too, is a matter because she as the 'experienced' (equals being old) should advertise fashion for the young generation.

Nick is released of jail and parks himself at Angela's garage. He has now become a writer and has already finished a book which everyone likes. Angela has also found a publisher for Nick's work.

Geoffrey invites Angela to a trip into the mountains. There he would like to ask her 'a question, which would change both's life'. But it's not the proposal Angela expected.

The parents' councils of Fairfield and Brooklyn organize a boxing match for charity causes. But Fairfield's boxer has to cancel - and Tony has to take his place. Angela coaches him for the bout.

Samantha thinks her boyfriend Chad is the cat's meow when he writes a song just for her. Word gets around, and the tune is heard by legend Ray Charles whom Angela coerces into recording it for her ad agency. When rat Chad starts seeing another girl, Samantha is so infuriated she demands the recording not take place. It takes a stellar performance of the song by Ray to make Samantha see that her friendship with Angela is more important than getting back at Chad.

Geoffrey keeps his brand new Porsche at Angela's while he's in Boston. After Angela has gone shopping using the car, she let the car outside. There the tree the neighbor's cutting down hits the car and causes a write-off.

Angela gives a surprise party for Tony because for the first time Angela's agency is in the black and it was Tony who persuaded her to open an agency of her own. As a present the painter Christos should portray Sam. Tony meets him and Christos tells him that a Marie Micelli once took painting lessons at him. This message causes a little crisis for Tony who now thinks he hasn't known his wife well enough.

Jonathan has a new girlfriend: Jenny. But Jenny has fallen more for Tony. When Jonathan finds this out he gets really upset.

Due to heavy snowfall life in Fairfield is down. To pass the time stories are told. Topic: Who has brought together the two families - Sam, cause she's the reason Tony wanted to move; Tony, cause he wanted to make life better for Sam; Jonathan, cause he needed someone who takes care of him; Angela, who needed someone for the household; or Mona, who has 'found' Tony?

As Tony doesn't want to sell his only 'Tony Micelli Baseball card', he tells Mr. Ferguson he has none. Angela, who has listened, now wants to get one for Tony. The trader Angela has asked calls Tony shortly after and offers him a lot of money which he really could need to buy Angela a Christmas present.

Sam has got into the school's basketball team. Her friend Todd hasn't and as she don't want to bother him she also goes without the team. Angela beats Tony in Miniature Golf.

Sam has had a big argument with Bonnie. Tony wants to see them both together again but Sam only agrees if he for his part makes it up with his old foe from high school, Mickey. Therefore Tony invites Mickey who has in the meantime become a Father. But when Tony annoys him too much Mickey strikes a blow.

For the weekend Angela goes to Maine with her friend Geoffrey. Tony now alone at home, the kids are on a school trip to Washington, invites his old flame Tanya. Angela and Geoffrey couldn't manage to go to Maine and return unexpected.

Jonathan, because he takes life too serious, should do something else than always studying. He decides in favor of gymnastics and Tony should teach him. During a competition he falls due to his overzealousness and breaks his shoulder. And this is something Angela really isn't happy about.

Dr. Ferguson, Marci's Dad, marries and Tony and Angela should be best man and maid of honor. In the course of this both have to face the question whether the want to marry again. At the wedding party they meet Geoffrey.

After a party Sam comes home with a love bite and Tony, beside himself, forbids her seeing Todd again. In the evening Sam sneaks out of the house to meet Todd anyway.

With a trick Jim Petersen snatches away Angela's first customer. Tony and Mona try, with a similar trick, to get him back to Angela.

Marci applies for the elite-school Montague. Sam also wants to do so and finds an advocate in Angela, a Montague Academy graduate. But Tony doesn't like the idea that Sam visits a school so far away.

Angela tries desperately to find a new job but no one of her old friends or partners has one for her. The only job she can find is one of a copy writer. Eventually, Tony and Mona convince her to open her own agency.

Overworked Angela goes to Mexico with the family, but when Angela's business loses an important account, Tony never gave Angela the message. When Angela comes home, she goes to the agency to learn that they lost the account. After sassing to her boss and telling him to chill, Angela loses her job.