Angela talks legendary performer Ray Charles into recording a love song written by Samantha's boyfriend as a jingle for an important account but when the young couple splits up, Samantha insists that Angela call the whole thing off. Ray Charles appears as himself.
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Charlie Brisco, Sam's old friend from Brooklyn, drops in to stir up some trouble, but is "discovered" by Trish Carlin, owner of a modeling agency Angela is using for a photo shoot.
After what appears to be a disastrous trip to Jamaica, Tony and Angela discover their true feelings for each other.
When Angela buys Tony a new car for his birthday, he realizes how attached he is to his beat up old van.
Samantha learns a valuable lesson when Tony catches her cheating on an exam and grounds her for two weeks.
Angela is shocked when an old boyfriend from college shows up to inform her that the Mexican divorce from their spur-of-the-moment marriage 20 years ago was never finalized.
Mona pressures Tony to set up a business meeting for Angela with his big-shot golf partner, never realizing that it could spoil Tony's new friendship.
During career week, Bonnie is such a hit at Angela's firm that Sam begins to think Angela likes her more.
Mona mends her flirtatious ways after Tony admonishes her for dumping an old friend of his after one date.
Angela arranges for Samantha to stay with her friend Trish Curtis, owner of a New York modeling agency, so that she can interview her four top models for a feature stony in her school newspaper.
Angela's and Tony's warm welcome to the new family next door turns down right chilly after Angela catches the neighbor's precocious little girl kissing Jonathan and Tony sees his beloved herb garden uprooted.
After Tony grounds Samantha for becoming intoxicated at a party, he is forced to re-examine his own views on social drinking.
The chance to meet none other than Mr. Frank Sinatra himself at a lavish gala sends Tony and Mona scrambling to compete for an invitation to attend with Angela but when Angela finds that she can't go, Tony and Mona decide to crash the event anyway.
After Angela is forced to hire an escort to accompany her to an agency function because she can't find a suitable date, Mona persuades Tony to ask her out on a "real date."
Tony's good intentions of spending a weekend skiing in Vermont -- alone with Samantha -- get snowed under when he meets a pretty instructor and Jonathan makes a grown-up decision to help his sick mom at home.
When Tony takes Angela to a Cardinal's reunion, a voluptuous baseball groupie from the old days throws him a few new curves.
When Tony has an unexpected reunion with his high school sweetheart, his patience is tried by her husband, who tries too hard to prove his superiority.
Waiting for her special birthday in restless anticipation, Angela reveals some secrets of her heart during a fit of sleep talking.
When Jesse invites Samantha to the prom, Angela's over-eagerness to make it a night to remember leaves Samantha wishing she could just forget the whole thing.
When Max pops the "big question" and asks Mona to marry him, Mona shies away from a wedding, until she is faced with a little competition.
Samantha is thrilled when a modeling job for one of Angela's ad campaigns leads to more work -- and money but Tony is terrified at the prospect of his model daughter living "life in the fast lane."
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