Lindsay is a local Stars Hollow teen, who attends Stars Hollow High with Lane and Dean, and attended primary school with Rory as well. She appears a sweet, regular teenage girl who has a good relationship with her family and a seemingly calm, nice life in Stars Hollow. She starts dating Dean Forester after his relationship with Rory ends, and they marry in 2003, but divorce a year later after Lindsay discovers that Dean cheated on her with Rory.
Lindsay bought Rory a magnet shaped like Mark Twain's head during their 4th Grade field trip to Mark Twain's house. Later, Rory wanted to pay her back, but Lindsay refused.
Lindsay is first seen when she runs into Rory at a high school hockey game, where they have an awkward conversation, but Rory doesn't understand why it's awkward. Not long after, Rory sees Dean, who is playing in the game, come off the ice to give Lindsay a kiss, and she realizes they're now together (hence the awkward encounter on Lindsay's part earlier). Rory expresses to Lane that she figured he would move on eventually, but had hoped he would pine for her. She states that Lindsay is a nice girl. Dean and Lindsay continue to date, and it can be assumed Lindsay is apprehensive about his friendship with Rory when she glances coldly at Rory during a town meeting. When Lindsay and Dean attend Kyle's party together, but the party ends on a bad note when Dean initiates a fight with Jess when he sees Rory crying. How Lindsay reacts to the obvious signs of protectiveness Dean demonstrates over Rory's feelings is unknown.
Despite this and being fresh out of high school, Dean announces that he and Lindsay are engaged a short while later. They marry in autumn 2003 and Lindsay's family is very helpful to the young couple in their first few months of marriage. Dean tells Luke that Lindsay's mom, Theresa, comes over to help clean up after dinner, and Lindsay's father, Thomas, frequently does house repairs. Lindsay's mother also spends time teaching Lindsay how to cook; although, it is seemingly unsuccessful. While Dean is working on construction at The Dragonfly Inn, Lindsay and Teresa bring him a warm lunch each day and they seem very happy together for a while, Lorelai commenting that 'Annette and Frankie really found each other'.
Lindsay decides she wants to get a townhouse sooner rather than later, which means Dean cuts back on college so he can work several jobs to afford it. When Lindsay is in the market, she overhears Rory discussing this with Lane, saying that if Lindsay wants a townhouse, she should be working too instead of making Dean drop out of college. Lindsay tells Dean about the incident and asks that he doesn't see Rory anymore. Whether or not she realizes that Dean does not listen to her demand is unknown. Realizing their marriage is quickly falling apart, Lindsay attempts to do what she can to repair it, such as making roast beef for Dean because it's his favorite meal. However, she does not realize that Dean has already done irreparable damage to their relationship and broken her trust by sleeping with Rory. It isn't until an entire summer has passed that she discovers the truth. She finds the letter from Rory in Dean's jacket that details their intimate time together, and she angrily and publicly chucks his belongings out their apartment window while the town watches. She files for divorce, and Dean moves back in with his parents. Lindsay and her mother run into Rory and Lorelai on the street. Theresa tells them both to go to hell, which is the last time Lindsay is seen. When Dean agrees to start a new relationship with Rory following these events, he mentions that he doesn't wish to parade their relationship in front of Lindsay or inconvenience Lindsay any further than he already has.
- Lindsay is a self-proclaimed bad cook, but she still tries. She even goes so far as to make roast beef for Dean twice because it didn't come out right the first time. She is so excited when it does work the second time that she jumps up and down, startling Dean who is carving the meat.