Linus and David Larrabee are the two sons of a very wealthy family. Linus is all work -- busily running the family corporate empire with no time for a wife and family. David is all play -- technically employed in the family business but never showing up for work, spending all his time entertaining, and having been married and divorced three times. Sabrina Fairchild is the young, shy, and awkward daughter of the household chauffeur, who has been infatuated with David all her life, but whom David hardly notices till she goes away to Paris for two years and returns an elegant, sophisticated, beautiful woman. Suddenly, she finds she's captured David's attention, but just as she does so, she finds herself also falling in love with Linus, and she finds that Linus is also falling in love with her.

Jenna is unhappily married, squirreling away money, and hoping to win a pie-baking contest so, with the prize money, she'll have enough cash to leave her husband Earl. She finds herself pregnant, which throws her plans awry. She bakes phenomenal pies at Joe's diner, listens to old Joe's wisdom, tolerates her sour boss Cal, is friends with Dawn and Becky (her fellow waitresses), and finds a mutual attraction with the new doctor in town. As the pregnancy advances, life with Earl seems less tolerable, a way out less clear, and the affair with the doctor complicated by his marriage. What options does a waitress have?

Kassie (Jennifer Aniston) and Wally (Jason Bateman) are best friends. Being unlucky in love, Kassie has decided to have a child using artificial insemination. Wally doesn't like this idea, but he isn't capable of admitting to himself, let alone to Kassie, that he's in love with her. At Kassie's artificial insemination party, Wally gets very drunk and spies the sperm donor's sample in the bathroom. Wally was way too drunk to know what he did that night, and Kassie has moved away because she doesn't feel that New York City is a place to raise a child. Now 7 years later, Kassie has moved back with her son Sebastian. While she is looking to get Roland (the sperm donor) more involved in their lives, Wally can't help but notice the many striking similarities that he and Sebastian share.

Angie lives in the Bensonhurst section of Brooklyn, N.Y. and dreams of a better life than everyone she knows. When she finds that she is pregnant by her boyfriend Vinnie, she decides that she will have the baby, but not Vinnie as a husband. This turns the entire neighborhood upside down and starts her on a journey of self discovery. This journey includes her family, a new lover and her life. Even her best friend Tina has trouble understanding Angie.