Soon after her divorce, a fiction writer returns to her home in small-town Minnesota, looking to rekindle a romance with her ex-boyfriend, who is now married with kids.

Rachel is a lawyer. When she was in law school she fell for another student, Dex, who comes from an affluent family, but she was too shy to say anything. When Dex meets her best friend Darcy, who sometimes treats her like dirt, Darcy makes a move on Dex and gets him. Eventually, they get engaged and Darcy asks Rachel to be her Maid of Honor. However, Rachel still has feelings for Dex and still can't say anything. Darcy throws her a birthday party and Dex is there. When she and Dex are alone she blurts out that she had a thing for him in college which surprised him, and after drinking a little they spend the night together. They try to forget the whole thing and agree that it means nothing. Ethan, Rachel's close friend, tells her that she'll spend her entire life regretting that if she does nothing.

Arthur is a happy drunk with no pretensions at any ambition. He is also the heir to a vast fortune which he is told will only be his if he marries Susan. He does not love Susan, but she will make something of him the family expects. Arthur proposes but then meets a girl with no money who he could easily fall in love with.

Brett, a young woman from the suburbs, is an associate editor at a small New York publishing house, hoping to be promoted when, on the same day, she meets a literary lion, Archie Knox, who's 50 and who shows an interest in her, and gets a new boss, a dolly-dolly Brit. Brett is soon dating Archie, then moves in with him. He's charming, attentive, and gives advice. He also has a history - ex-wives, a distant daughter, a couple of diseases, and a photo album of former girlfriends. It's no fairy tale: family issues (and more) intervene, and Brett has decisions to make. Meanwhile, she's working with a writer who fears peanut butter sticking to the roof of his mouth. Is Archie dinner, an hors d'oeuvre, or a peanut-butter sandwich?