Because she is enjoying a vacation in Mexico, Angela misses the meeting for an important account and gets fired.

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Angela starts looking for a new job, but has trouble finding something she is suited for the best. When she settles for a job as a copywriter, Tony and Mona encourage her to start her own company.

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When her best friend Marci applies for a highly expensive private school, Samantha wants to apply as well. This gladdens Angela, but worries Tony.

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Tony and especially Mona stretch Angela's theory you must spend money to make it in business, while she wines client Ping in San Francisco, by celebrating the account in advance. They also fall for a limo company's sales pitch to lease for $1,000 a month. Angela failed and wants to economize. Tony and even Mona try to make the limo earn its keep. That works poorly, until Ping unsuspectingly rents it, driven by Mona.

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Sam has a date with a guy whom every girl wants. The next day she's acting very strangely. Tony discovers that she has a hickey. When she says it's not a big deal and that she has another date with the guy, Tony grounds her. Angela and Mona tell him that he should talk to her. He does but she refuses to see Tony's side. She then sneaks out for her date.

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Tony and Angela are both asked as paranymphs at a wedding of common friends. The romantic atmosphere and table conversation with other wedding guests stir dreams of marrying themselves and make them take stock of mutual feelings as Tony's curious housekeeper position is challenged and defended.

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Jonathan brings home more straight AAs, yet a teacher writes in a letter an extracurricular activity should broaden his perspective. Tony convinces Angela that the only way to avoid a nerd label is joining a sports team, accepted only if he coaches personally, and the boy picks gymnastics. The training goes great, while Angela drives secretary Mona nuts with workaholic zeal for her new agency. Jonathan takes a painfully excessive risk, yet Angela blames Tony for his shoulder dislocation until Mona explains the parental example pressure syndrome.

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Geoffrey Wells gets Angela to agree to a weekend in Maine, so Tony digs up his dusty black book and finds an eager date, Tanya Stromball. When bad map reading made the Maine voyagers return, Tony feels crammed and says he'll take her to their native Brooklyn, but stops in a fancy inn. Coincidentally, Anela and Geoffrey end up there too, next door, well, balcony.

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Tony gets a visit from Callahan, a horrible chap he constantly fought with in Brooklyn. To his amazement, the fiend is now a priest, but as soon as they start teasing again things get out of hand, even literally: hard-handed. Tony gets commandeered by the bishop to help out in a home as father Callahan left parish service, feeling he obviously remained a sinful scoundrel. Tony tries to mend that feeling as well as the dinner.

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Tony nor Angela would admit it, but they're competitive enough about mini-golf to sneakily practice in secret after she won their first try and agreed to a rematch. Tony is puzzled when Sam squanders her chances on the basketball school team to spare a hunky kid, but Angela's sob-story changes her mind. Now Sam fears she lost the boy.

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Tony prepared a wonderful Christmas goose dinner, but Angela accepts to join Geoofrey's family's catered dinner. Geoffrey also scares Tony from giving Angela his hand-made gift by buying her diamond earrings. Tony lies to have none of his own baseball cards left to avoid it being snapped up by Dr. Doyle Ferguson. Angela feels restoring that part of his past is the right gift for Tony. The scumbag dealer she buys it from actually bids on Tony's, tempting to pay his own 'worthy' gift for her.

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The kids's school closes and Angelo's train doesn't ride due to excessive snow. Whle everyone cuddles up by the fire, Tony tells how he decides to seek a janitorial position so he could afford moving from cramped Brooklyn to Connecticut. Mona picks up how they met and she convinced him and later Angela that Tony as housekeeper, replacing 'Nazi nanny' Hiller, and as father-figure for Jonathan, would be ideal for both families and suit her own hunk-sighting lust.

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Jonathan starts seeing a girl named Jenny, but she is more interested in Tony. Feeling betrayed, Jonathan is determined on taking revenge on Tony.

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While everyone is planning a surprise party for Tony, Tony starts suspecting his late wife had an affair during their marriage.

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When Angela accidentally destroys her latest boyfriend Geoffrey's new expensive car, he immediately breaks off their relationship. However, he later regrets his decision and contacts Tony to help him win Angela back.

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Samantha is excited when Ray Charles, Angela's latest client, wants to use a song Sam's boyfriend Chad wrote especially for her. That is until she catches Chad cheating on her.

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With high expectations, Tony enters a boxing competition, with Angela as his intimidating coach. Little does he know how professional the other contestants are.

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Angela feels Geoffrey will propose to her and starts to doubt about whether she will accept or not. Mona and Tony both feel she deserves better.

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Nick is released from jail and visits the Bower-Micelli residence. Tony soon finds out that Nick is writing a book with double motives.

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Tony's new girlfriend Casey offers Angela a new commercial for footwear. Angela, though, is rejected for being too old. Hurt, she undergoes a make-over to look younger, which shocks the family.

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Mona convinces Tony to let Samantha stay out all night for a concert. Inspired, Angela makes a list of spontaneous things she wants to do. Tony encourages her, until he finds out she is dating the former high school wild man.

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Mona is less than happy about Angela's new assistant, Fiona Finch, who seems to be the perfect worker. Meanwhile, Tony is reluctant to visit the dentist.

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Mona goes to visit her brother who bought an old hotel. And he also used money that's hers. And she discovers that the place is a money pit.

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Tony tries to relive his wild past when Mona offers him to move into her apartment, as she is leaving to run her brother's hotel. He soon finds out that living careless is not all that satisfying.

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