Lindsay Lister: Rory Gilmore’s Biggest Victim In Her (Multiple) Cheating Scandals – And Exactly Why She Deserved So Much More Than She Ever Got From Her Short-Lived Marriage To Dean

Growing up, I used to think that cheating was the only reason for two people to break up in a relationship. Most likely it’s because it’s seen as the biggest, most dominant reason for a breakup on TV and film. It’s often used for dramatic convenience rather than as a realistic reflection of a relationship’s nuanced end. Infidelity serves as a reliable and familiar plot device to create conflict and garner audience sympathy. To break it down more thoroughly:

The dramatic functions of infidelity

• Easy source of drama: Infidelity is a powerful and instantly recognizable source of conflict that can be easily injected into a storyline to prevent the audience from getting bored with an otherwise happy couple. In contrast to real life, which has many mundane reasons for relationships to end, cheating offers high-stakes interpersonal drama that moves the plot forward quickly.

• A “bad but not irredeemable” action:Writers can use infidelity to show a character’s flaws without threatening their place in the show. Unlike illegal or violent actions that might require the character to be written out, cheating is a dramatic but often forgivable personal problem. This allows the character to remain a central figure, even if they must navigate a redemption arc.

• Character development and audience manipulation: A cheating storyline can be a shortcut to make an audience feel sympathy for the betrayed partner, placing them in a vulnerable and emotional state. It can also add complexity and moral ambiguity to a character’s arc, sometimes portraying their cheating as an understandable reaction to an unhappy partnership, such as in The Office or Sex and the City.

• A catalyst for other characters: Infidelity can act as a narrative trigger, not just for the central couple, but for the relationships of those around them. This is especially true in ensemble casts where a single affair can send ripples of drama through the entire group. 

Infidelity as an overused trope

The frequent use of cheating storylines in media, particularly as an unambiguous reason for a relationship to end, is often criticized as “lazy writing”. Many romantic comedies, for example, rely on a cheating partner to make one half of a couple seem unlikable and pave the way for the protagonist’s “true love,” even if a simpler and more honest breakup would have been more mature and realistic. 

Examples of this often-criticized trope are found across many genres:

• Romantic comedies: A character often cheats with their charismatic ex-partner, creating a contrived dilemma that forces them to choose between their old flame and their current, more stable (but “boring”) partner.

• Drama and ensemble shows: Infidelity is a common engine for conflict, as seen in shows like Grey’s Anatomy, The Good Wife, and The Affair. In these narratives, the aftermath of cheating often drives seasons-long plots focused on trauma, reconciliation, and revenge.

• Friends (“We were on a break!”): The iconic storyline of Ross and Rachel’s breakup, which hinges on Ross sleeping with someone else during their separation, has become a famous example of how central and debated a cheating storyline can be. 

Nuances and consequences of on-screen infidelity

While often used for simple drama, some narratives explore the complexities of infidelity, portraying it not as the root cause of a split, but as a symptom of deeper issues within the relationship. These more nuanced portrayals acknowledge factors like: 

• Emotional neglect
• Long-standing unhappiness or boredom
• Geographical separation 

This approach reflects how infidelity works in the real world, where it is often the final blow to an already fractured relationship. Friends co-creators had plans to create a storyline where Chandler would cheat on Monica when the entire gang went to Vegas. Thankfully, the entire idea for this ridiculous storyline was completely scrapped when Matthew Perry, who played the lovable, funny man, refused to oblige as he felt Chandler would never do such a thing to Monica.

One show that didn’t shy away from storylines that involved cheating in relationships was Gilmore Girls. More particularly, Rory’s character arc. Cheating wasn’t just a one-time thing that happened to her. It somehow became an essential element in her story. It happened multiple times – with multiple people. She wasn’t ever cheated on, though she saw it otherwise. She was the cheater, and she was the ‘other woman’. Two of these situations involved Dean, her first boyfriend. The first time was when she cheated on him with Jess, Luke’s nephew, who ended up being her boyfriend later on. The second event happened when Dean cheated on his wife, Lindsay, with her.

The first time Rory was involved in a cheating game was when Jess came to live with Luke. He was a ‘bad boy’ with a bad reputation, but he had a lot in common with Rory. They both shared the same love of books, and it kept them connected. More so than her and Dean. By the point that Jess came to Stars Hollow, she and Dean had been together for a year. They were solid. It wasn’t that they were drifting apart by any means; but rather that she was attracted to Jess; more than she was to Dean. She tried to deny her growing feelings for Jess. She tried telling herself that he was just a friend to her. But the more time they spent together, the more her feelings grew stronger for someone that wasn’t her boyfriend. Dean, in turn, saw right through both of them and what was happening between them when they thought he wasn’t looking. He tried telling himself that it was just a crush on Rory’s side; that it’d pass. But eventually, he just couldn’t take it anymore.

Dean broke up with Rory in the middle of the dance floor. He yelled at her; telling her she was free to be with Jess. It was that night that Rory and Jess finally admitted their true feelings for one another and became an official couple. As soon as they got together, however, their relationship was severed and filled with tears, jealousy, misunderstandings, and anger. They loved each other, obviously. But they weren’t right for one another. After Jess left town without telling her, Rory tearfully broke up with him over the phone when he called her without saying a word. She was the only one talking until she had nothing left to say.

During his and Rory’s time apart, Dean got closer to Lindsay, his high school classmate that Rory also knew before she moved schools. Despite them breaking up, Dean showed great care towards Rory. He even defended her when he found out that Jess forced her to have sex and got mad when she declined his advances. Soon after starting to date Lindsay, Dean proposed. It was a happy ending…or at least it should’ve been.

Following the official end of her relationship with Jess, Rory started college. She became wounded and insecure in its aftermath, and the new, what should’ve been an exciting time in her life, became crash course with her past. As they started spending more time together and grew closer, Rory became increasingly jealous of Lindsay. To her, Lindsay embarked on a life’s journey ahead could’ve had with Dean had she not messed things up and cheated on him with Jess. It was as though she saw her entire relationship with Jess and everything she shared with him as a mistake. Seeing Dean seemingly happy with someone else makes Rory jealous of the attention Lindsay received from her former love.

Alas, Dean’s friendship with Rory wasn’t just platonic. The day before he was set to get married, he ducking admitted during his bachelor party that he was still in love with her. Nevertheless, he married Lindsay. Rory was there from afar looking ever so heartbroken. But Dean marrying another woman didn’t stop him from getting closer to Rory. In hindsight, their affair was foreshadowed for the entirety of season 4. The tension between Dean and Rory was gradually built, with scenes like her calling him on spring break and him returning that call, the pair talking while he was working at the inn, and her outrage at him not going to college. Dean saying Rory was the only one who really cared about what was best for him even though he had a wife at home who gave him everything he wanted and more was, with hindsight, a pretty clear turning point.

Their feelings grew stronger for each other and their egos became more comparable to rhododendron. Dean was never likely to leave Lindsay since, while he was always portrayed as somewhat dim-witted, he knew that Rory wasn’t about to change her life plans to accommodate living in Stars Hollow with him. Dean was looking for a woman in his life who’d be a caretaker. He wasn’t looking for a career-oriented woman like Rory aimed to be. He wasn’t looking for a woman who’d be a housewife who’d cook, clean, and care for all his needs at home. Lindsay was the representation of exactly what he was looking for. Her only responsibility as Dean’s wife was take care of him and his home, and she did exactly that.

And yet, no matter what Lindsay did for him, she still didn’t do enough, and that was solely because she wasn’t Rory. He was obviously not happy in his marriage, simply due to the fact that his wife wasn’t Rory. Rory was just as in love with Dean as he was with her. When talking about her relationship with Lane, her best friend, she said, ‘I think I really blew it there, you know? I didn’t appreciate it. I always knew that no matter what happened, he would be there.’ This was her comparing her relationship with Dean to that of Jess, saying that Dean was her safe space whereas Jess was unpredictable and unreliable.

Dean and Rory’s lingering feelings for one another only grew stronger, and in time, they eventually slept together, with it being Rory losing her virginity. Rory, always portrayed as ‘special’ and ‘smart’ by her mom and grandparents, really didn’t think things through when she decided to have sex with Dean. When first met Dean in the pilot episode, she made a joke in which she said, ‘Maybe I just didn’t look up because I’m unbelievably self-centred.’ But in that particular situation, she most certainly was. When Lorelai, Rory’s mother, came home and walked in on her and Dean post the deed, Lorelai l, perhaps maybe for the first time in Rory’s entire life, confronted her. Like, truly confronted her; telling how wrong she was for doing what she did. Instead of seeing things from her mother’s perspective, she saw it as her mother ruining her experience for her. She acted as if she was entitled to sleep with Dean even though he was married to Lindsay because, in her words, he was ‘MY Dean first!’

Gosh, that pissed me the fuck off. Lindsay was made to be the villain in this entire storyline when, in reality, she was the only one hurt in the situation. Her character was created as an obstacle between Dean and Rory and make their affair seem more dramatic. The writers intentionally made her a one-dimensional, unlikable character who was portrayed as lazy and demanding, rather than a fully developed person, to simplify her role as a plot device.  To break it down more thoroughly:

• Obstacle for the main couple: Lindsay’s marriage to Dean became the primary conflict standing in the way of him getting back with Rory. By making her unsympathetic, the show made it easier for viewers to root for Rory and Dean to get together. 

• Character-driven vs. plot-driven: From the show’s perspective, Lindsay served a specific plot purpose rather than having her own fully realized story arc. The writers chose to focus on the dynamics between Lorelai, Rory, and Dean, which often came at the expense of showing Lindsay as a nuanced individual. 

• Portrayal as unmotivated: The show presented Lindsay as a spoiled housewife who expected Dean to provide for her, contributing to the perception that she was a poor partner and therefore a villain. She was shown as not working or going to college, which, combined with her desire for a townhouse, made her seem materialistic. 

• Dean’s actions: Dean’s affair with Rory was a major turning point, and making Lindsay the “villain” provided a simple explanation for his infidelity. He was portrayed as being stuck in a loveless marriage, and cheating with Rory was the way he ultimately escaped it. 

• Misogynistic undertones: Some viewers and critics have argued that the portrayal of Lindsay is an example of misogyny, as she is reduced to a caricature to serve the male characters’ needs. From this perspective, she is seen as a trophy wife whose only purpose is to be a plot device to drive Dean’s story. 

Rory didn’t feel guilty for having slept with Dean multiple times while he was married to Lindsay, but she did break things off with him. She wrote more him a letter and asked Lorelai to give it to him while she was away travelling with her grandmother, Emily, in Europe. In it, she wrote that their night together was special, but he was married, so until he figured things out for himself, she was getting herself out of the situation. It was a nice letter, at least according to Lorelai. The letter was meant to only be seen by Dean, but Lindsay found it, and that was how she found out about the affair.

Distraught, Lindsay ended her marriage to Dean – and very publicly, might I add. The entire town heard their breakup, and it was certainly what everyone was gossiping about that particular day. She threw ‘a fit’. While at their home, she threw all of his things out the window, screaming that their marriage was over. Dean, in turn, tried to salvage his actions by telling her it was all a mistake, but she knew better than that. The marriage was officially over. When Lindsay was seen again with her mother, her mother put the entire blame for the divorce on Rory. She explicitly yelled, ‘Lives were DESTROYED!’ While defending her daughter, Lorelai said that she didn’t break up a marriage. As Lindsay’s mom told both Rory and Lorelai to go to hell, she and Lindsay ran off from their awkward run-in, and that was the very last time we ever saw Lindsay.

Having moved back home with his parents following his separation with Lindsay, Dean put all the blame for it on Rory; much like Lindsay’s mom did. While I totally agree that she played a big role in it, it wasn’t as though Dean declined her advances. After all, it takes two to tango. And not only did he cheat on her in a physical sense, but emotionally too. He didn’t actually love Lindsay. But rather, he loved the idea of her. She was the ideal woman that he was looking for. But this in itself wasn’t a good enough reason to marry her. It seemed like all Dean was doing was use her to fill a void that was missing in his life, and that was Rory.

In many ways, the way Dean treated Lindsay could be compared to how Rory treated Dean during their high school days. You know, when Rory emotionally cheated on Dean with Jess and then got together with him as soon as Dean broke up with her. But people tend to forget that Dean and Lindsay were MARRIED. And yes, they did get married too young, fresh out of high school, but nevertheless, it doesn’t change the fact that they were married. This likely happened due to Lindsay’s way of life. Her family seemed more Stepford than Stars Hollow with their ideals, and it probably put the idea of marriage in Lindsay’s head.

Dean’s marriage to Lindsay mirrored a marriage we’d see in the 1950’s. He was working two jobs to make ends meet, and she stayed home and took care of the house, as well as him when he was home. She was doing her best; trying SO hard to make him happy and be the wife he wanted her to be. Lindsay was his dream girl – on paper. She never had big dreams of going to an Ivy League school and becoming a world-renowned journalist like Rory; she wanted to settle down and have a quiet domestic life, and this was exactly what Dean was looking for. In a way, Dean marrying her was his way to convince himself he was rightly and truly over Rory. This was a terrible reason to get married, and unfair to Lindsay.

The last time we ever saw Lindsay, she let her mother do the talking for her – about how LIVES WERE DESTROYED! It was where both mother-daughter duo have a dramatic run-in and the mothers did all the talking. Lindsay and Rory stayed mum – barely looking at each other. She had every right to hate Rory for her part in the marriage breaking down, but honestly, not enough blame was put on Dean. Not only did he cheat on her, but he constantly disrespected her, belittled her, and made her feel less than; like she wasn’t good enough; like she was constantly did something wrong. The scene where he berated Lindsay for answering his phone was absolutely painful to watch, and she was left scrambling to pick up the pieces of their marriage, completely left in the dark as to why it’s failing in the first place. In a way, Lorelai was right – Rory wasn’t the one who broke up the marriage. It was Dean.

That’s not to say that Rory wasn’t to blame for her part of the tragic tale, but nevertheless, Dean was MOSTLY responsible for how things turned out. And maybe – just maybe – Lindsay should’ve been the one who confronted Rory instead of her mother. Maybe Rory would’ve actually taken accountability for her actions and apologized to her. Maybe then Rory’s personal life wouldn’t have continued to revolve around cheating even years after what had happened to Lindsay at the hands of Rory and Dean. I personally wish we saw more of Lindsay. The actress behind the character, Arielle Kebbel, thinks so too! She even said she wanted to see a spinoff show with Lindsay as the main character. She said, ‘Honestly, you know what I think Lindsay would say? She would be like, #IGotMarriedTooYoung. They were like 18, in the show, when they got married. What do you expect? I think she deserves a spin-off. For f**k’s sake, she still deserves her day in court, as far as I’m concerned.’

Once there was no obstacle standing in their way, Rory and Dean became an official couple (again). Not everyone was on board for the happy couple, especially Luke, who by that point, was dating Lorelai and therefore had to spend more and more time with the newly reconciled couple. Luke knew that Dean was still in love with Rory when he married Lindsay. Dean’s confession to Luke at his bachelor party, followed by his affair with Rory, confirmed Luke’s negative view of Dean’s character. In Luke’s eyes, Rory was brilliant and had a bright future, while Dean was immature, didn’t know what he wanted, and lacked ambition. Luke felt that Dean was holding Rory back and destroying her dreams. This was very much in contrast to Jess, whom Luke at one point supported for Rory, viewing him as a good intellectual influence.

In an attempt to make things ‘right’ and go back to the way things were before, Rory and Lorelai plan a double date with their respective boyfriends. During that date, Luke’s hostility toward Dean is explicitly shown. Luke couldn’t hide his contempt and openly antagonized Dean, creating a miserable experience for everyone. Having been a constant presence and a reliable figure in Rory’s life, Luke acted like a protective father, especially after becoming romantically involved with Lorelai. He believed no boyfriend was good enough for Rory and felt that it was his role to protect her from heartache. Knowing the years-long history between her and Dean, he didn’t feel that Dean was good enough for her.

The newly rekindled relationship between Rory and Dean just wasn’t the same anymore. No matter how much they tried to make it work, it wasn’t the same. They didn’t have the same spark as they did before. They didn’t have the same chemistry they did before. Everything between them seemed to be forced. Things were obviously not working. They were too different this time around. Rory was living her life at Yale. With Dean, she was holding on to her past that was so irrelevant to her by that point in time. Dean’s constant insecurities controlled their relationship, and propelled their final breakup. He didn’t have much ambition for a life outside of Stars Hollow, which was the complete opposite of Rory. Dean loved her, but his love was conditional.

They both eventually realized that their time together had expired. As Rory was getting closer to Logan and his friends, she was slowly drifting apart from Dean. As much as he was aiming to hold on to what he and Rory once shared together, he realized that he didn’t belong to Rory’s world anymore after he picked her up from a gathering her grandparents had planned for her and he saw her with her new crowd. In one last attempt, he asked her if he belonged there. Rory, tearfully, looked down and didn’t say a word. She knew that it was over between them. She just didn’t want to say it. She didn’t have the words to say it out loud.

When Dean reappeared in the Gilmore Girls revival, we learned that he was married to a woman that was neither Rory nor Lindsay and living the life that he always envisioned for himself. This was honestly so, so sad. It made me think of Lindsay. It was the life that she envisioned for herself too. It was the life that she envisioned for herself with Dean, but Dean didn’t have the guts to do right by her and tell her the truth – that it wasn’t the right time. I hope that wherever Lindsay is, she’s happy, and that she’s living her life the way she’s always wanted…