- See also Minor Characters in Lindsey's Story
- Lindsey Bergman
- Mr. Tiny: Lindsey's dog
- Miss Kinney: Lindsey's teacher
- Mr. Nelson: the school principal
- Josh Thompson: classmate
- Mrs. Bergman: Lindsey's mother
- Ethan Bergman: Lindsey's brother
- Gordon Bergman: Lindsey's father
- Rhonda Bergman: Lindsey's aunt
- Bernie Bergman: Lindsey's uncle
- Mrs. Schumacher: Lindsey's nosy neighbor
- Mr. Pringler: Lindsey's band instructor
- Blair Kolinski: the class bully
- Missy Rizzo: another class bully
- April Greely: Lindsey's best friend
- Mrs. Thompson: neighbor and mother of Josh Thompson
- Sophie: Lindsey's cousin
- Miss Andersen: the school librarian
Chapter by Chapter Summary
Chapter One: Over the Line
Lindsey introduces herself as the person who ruined one of the most important days in her family's life. Her story starts when she is hit by a Matzo Ball at her brother's bar mitzvah. Lindsey flashes back to how she came to the point where she was hit with the Matzo ball, and thus begins Lindsey. Lindsey's first incidence of wrongdoing is when she tries to end the school Pet Parade. Lindsey is so angry at the indignity of dressing animals up in human clothes that she passes out fliers and prepares a speech. But no one takes her seriously and Miss Kinney, her teacher, will not let her make that speech. So Lindsey employs drastic measures by kidnapping Josh Thompson's iguana and climbing up a tree. The Pet Parade is over, but Lindsey finds herself in big trouble. Her mother makes her write a letter of apology to Josh Thompson and takes away Lindsey's prized scooter. Lindsey is still confused and does not know what she did wrong. At dinner that night Lindsey's father makes the announcement that Aunt Rhonda is planning on divorcing Uncle Bernie. Uncle Bernie now has nowhere to go and will be moving in with the Bergmans while his divorce is finalized.
Chapter Two: A Great Day
Lindsey meets up with Mr. Pringler, her band instructor, who tells her that she is doing good on the trumpet. Lindsey asks him if he has a girlfriend; when Mr. Pringler says no Lindsey can't stop thinking about poor, lonely Mr. Pringler, who has no one to take care of him. Suddenly Lindsey becomes a matchmaker, looking for prospects for her band teacher. On her way home Lindsey encounters April Greely, who is being picked on by school bullies Blair Kolinski and Missy Rizzo. Lindsey walks April home and discovers a new friend. When Lindsey comes home, she discovers a glum and unhappy Uncle Bernie, who has been home all day moping over his divorce. To try to cheer him up, Lindsey lends him her scooter despite his protests. Uncle Bernie rides down the street on it before Mrs. Thompson yells at him and he falls over, nearly injuring himself. Lindsey receives a lecture from Mom on how coercing Uncle Bernie to ride the scooter is not a good idea, and Chapter 2 ends with Lindsey being annoyed at her parents being preoccupied by her brother Ethan's bar mitzvah.
Chapter 3: What a Mess!
Lindsey finds April Greely being picked on again, and this time stands up to the bullies herself. One of the bullies rats her out to Miss Kinney and Miss Kinney makes Lindsey stay after school. Lindsey then decides while helping set up the Perfect World Collages that Miss Kinney would be a perfect match for Mr. Pringler and so she conspires to set the two of them up. Lindsey comes home to find that Uncle Bernie accidentally threw away her Perfect World collage pictures and she has to start over. The entire family and April team up to help Lindsey come up with a new collage.
Chapter 4: A Not-So-Perfect World
The Bergman family encounters some snags with Ethan's bar mitzvah. First, Aunt Rhonda wants to invite her new boyfriend to come, and secondly, the pressures of practicing Hebrew have finally caught up with Ethan, and as a result he breaks out in acne all over his face. Lindsey and April are cornered by the two bullies and Josh on the way to school; Lindsey evades them by referring to Josh by the nickname his mother calls him (Joshy). Phase II of Operation Pair off Miss Kinney and Mr. Pringler goes into action. Lindsey and April continue to scheme to pair the two up. Lindsey then has an epiphany regarding the green ugliness of trash cans and takes her mother's smiley face stickers and puts them all over every trash can in the neighborhood. Planning for Ethan's bar mitzvah continues, with Lindsey and her mother sorting out guests and trying to figure out who goes where, especially now that they have the added awkwardness of Aunt Rhonda and her new boyfriend. Lindsey loses the Perfect World Collage contest to Blair Kolinski and breaks down in tears in the bathroom over her loss. Lindsey's troubles only get worse when Mrs. Schumacher, the nosy neighbor, reports Lindsey to the police for putting smiley faces all over the trash cans in the neighborhood. Lindsey gets into bigger trouble and has to write letters of apology to every neighbor whose trash cans she defaced with her smiley face stickers.
Chapter 5: Rock Bottom
While planning Ethan's bar mitzvah, Lindsey comes up with the idea to pair Uncle Bernie up with her cousin once removed (mother's side, so they're not related) at the bar mitzvah. Lindsey's plotting and scheming regarding her teachers and now her uncle continues, until she comes home from school to find Mr. Tiny has disappeared. Lindsey makes a Lost Dog flier and peppers the neighborhood with them while searching for Mr. Tiny. The conclusion of Lindsey's plot to pair up her teachers occurs after she tells Mr. Pringler to buy Miss Kinney some tulips. When tulips show up at her teacher's desk, Lindsey finds herself in big trouble. Miss Kinney is actually engaged; there's no ring because she's allergic to metals and Mr. Pringler is embarrassed to have found out that he has been pursuing an engaged woman all along. After Lindsey finds out how badly her attempt at matchmaking went, she feels that her life has hit rock bottom. The worst is yet to come, however, when Lindsey gets into trouble with her mother yet again. Mom tells Lindsey to stop meddling in people's lives for good.
Chapter 6: Forgiveness
Lindsey is woken up early in the morning to find that Josh Thompson found Mr. Tiny while on his paper route. After his safe return, the Bergmans plan the last of the bar mitzvah preparations. On the day of the bar mitzvah, Ethan has a breakdown and won't let anyone see him but Lindsey. Tired of meddling and getting into trouble, Lindsey marches to her room and leaves Ethan alone. Uncle Bernie finally convinces Lindsey to help her brother, telling her that there is a difference between matchmaking and helping someone who needs help. Lindsey persuades her brother to go through with his bar mitzvah, after reminding him that sometimes people need to make mistakes and then reminding him that his Hebrew is just fine. While at the bar mitzvah, Lindsey finds out why cousin Sophie was not invited: she was the person who encouraged Aunt Rhonda to break up with Uncle Bernie. Sophie and Bernie get into a big food fight and that is when Lindsey is hit with the Matzo ball. Lindsey breaks down in tears and feels like an idiot, until April tells her to make it right. Wondering how to do that, Lindsey asks April how. April tells her to start with Uncle Bernie. Lindsey apologizes and confesses her role in Sophie's appearance and Uncle Bernie forgives her and asks her to dance. While they're dancing he tells Lindsey that she's not a worm, or a failure, that sometimes you have to fail before you succeed, and despite her failures, Lindsey is still loved.
The True Stories section focuses on three real American Girls who are trying to make the world a better place. The first girl is Hilary Staver, who raises money for the World Wildlife Fund to save tigers. Determined to help out, Hilary's efforts were recognized by her local newspaper and then by the head of the World Wildlife Fund. Brita Thomas of Minnesota started a fund to provide gym shoes to needy children so that they can participate in gym class. Austyn Lindsey of Florida learned that manatees were dying because people were speeding in their boats on the Florida coast. Determined to make a difference, they raised money to raise awareness of the plight of the manatees. As of the publication of Lindsey they have yet to be successful.
- A girl by the name of Caitlin Rose Ward was the model for Lindsey.