When Dean and Rory broke up over Jess, Rory was surprised to see how quickly Dean moved on. And he didn't just move on with anyone; he began dating her stunning former classmate, Lindsay Lister. Lindsay and Dean seemed like the perfect match on the outside in Gilmore Girls. They were both tall and gorgeous and seemed happy, but deep down, viewers knew Dean's heart always belonged to Rory.
Dean and Lindsay would eventually go on to get engaged, married, and divorced. As cute as they could have been, there were a ton of red flags that the two of them chose to ignore. Dean and Rory's affair didn't help his marriage to Lindsay, but was Rory the only reason why this marriage didn't work?
Perfect Together: Young & Smitten
The first time viewers got a glimpse at Dean and Lindsay's relationship was at Dean's hockey game. After the game, Dean skated over to Lindsay and gave her a sweet kiss. The two seemed so happy to be together. Rory watched the public display of affection from afar and felt indifferent about the relationship. She always knew he would move on but deep down inside, she always wished he would stay single and fight for her (which, of course, is unfair considering she was with Jess).
At this moment, Dean and Lindsay were young, smitten, and in love.
They Were Awful: Was Dean Only With Her To Get Over Rory?
When Rory and Dean broke up, she went directly to Jess. That's why Dean ended the relationship in the first place, because her feelings for Jess were so obvious that it was embarrassing. Jess and Rory took it slow but she never had a chance to grieve the loss of Dean because she was already in another comfortable relationship.
With Rory clearly happy, Dean most likely did what any teenager does: go on the rebound. Lindsay could have been a perfect distraction for Dean. He was finally with someone who went to the same school as he did and actually had time for him. She was everything Rory wasn't. But that's hardly a sustainable foundation for a relationship.
Perfect Together: Lindsay Was The Kind Of "Wife" He Pictured Himself With
In the episode "That Damn Donna Reed," Dean and Rory got into a disagreement over the roles of women in the household. Dean respected the modern-day working woman but he was accustomed to having a stay-at-home mom and appreciated it while growing up. He too wanted a wife that welcomed him with a big hug after work and had a hot dinner waiting for him. Rory proved to him how silly that was in the modern world but Dean only liked what he knew.
When he married Lindsay, he got exactly what he wanted. She was the stay-at-home wife who took care of the house and made his favorite foods. What he didn't realize, however, was how tiring working three jobs was just to support their lifestyle.
They Were Awful: It Was "Her" Wedding & Household
It's hard to look past Lindsay's ignorance when she married Dean. Like Dean, she wanted the cookie-cutter life as a homemaker who managed the household while her husband was hard at work. But she was clearly too young and delusional to realize how out-of-touch her dreams were.
Dean was working three jobs and was exhausted. She pushed him to buy a townhouse by the end of the year, which meant he had to stop going to school just to fulfill her dream. Likewise, when Dean and Lindsay were planning their wedding, Rory accidentally said it was "Lindsay's wedding" instead of their wedding. Sadly, Dean agreed with her — it was all about Lindsay.
Perfect Together: Loyal To Stars Hollow
When Dean and Rory began dating after he divorced Lindsay, one of their disagreements was the distance between them. Rory was a college student at Yale and wasn't always in Stars Hollow. After college, Rory was obviously going to graduate and move on to greater things. Was Dean willing to move away from Stars Hollow to be with her? And would Rory even want Dean to move with her?
Dean and Rory never made it long enough to have that conversation but it was obviously a perk in his relationship with Lindsay. The couple was dedicated to the small town that made them and they enjoyed living there together.
They Were Awful: He Was Emotionally Vindictive
Dean was so upset with himself that he took his frustrations out on Lindsay; some would even say that he was mentally abusive. He made his wife feel like she was worthless, which only made her try harder in their relationship while he was checked out.
When Dean and Rory slept together for the first time, he came home to find out that he left his cell phone at home and that Lindsay answered it when he was gone. Dean freaked out on her and told her that she didn't respect him... but didn't he just cheat on her?!
Perfect Together: Her Family Took Him In
For as small as Stars Hollow is, Gilmore Girls fans never meet Dean's parents! We've met his sister and seen his house, but why were his parents MIA?
Regardless of the case of the missing parents, when Dean and Lindsay get engaged, he told Luke at the arcade that Lindsay's parents were the most selfless people he's ever met. They took him in and treated him like he was their own son. It seemed like things finally worked out for Dean. Luke was happy that Dean was in a good place (even though he knew deep down that Dean was still pining over Rory).
They Were Awful: The Affair
One of the worst parts about Dean and Lindsay's marriage is that he cheated on her with his ex-girlfriend and keeper of his heart, Rory. It makes fans wonder if Dean even loved Lindsay or if he was only with her as a distraction that went too far. There are even theories that Lindsay was pregnant, which is why they got married so quickly (but the pregnancy never made it to fruition).
No matter the reason why they got married so quickly, Dean's affair proved that his marriage was broken and that he and Lindsay were not perfect together.
Perfect Together: Visiting Him At Work
This coincides with Dean's vision of having a Donna Reed kind of wife. While Dean was working in construction, he got a job fixing up Lorelai's Dragonfly Inn.
When Rory came to visit the inn's progress, she saw Lindsay deliver lunch for not just Dean but most of the construction team. This vision of generosity and love made Rory rather envious. Dean was being catered to while working hard for his future to support his wife. The couple was getting everything they both wanted out of their marriage at that moment.
They Were Awful: They Didn't Inspire Each Other's Future
When Dean and Rory were together, Dean was happy staying close to home and going to community college. Higher education wasn't really at the top of his list. When they broke up, Dean decided to focus on himself and apply to a larger state school, which he happily got into and attended.
Sadly for Dean, his dream of making something of himself through school died when Lindsay practically forced him to drop out. She wasn't working and wanted a townhouse. This is why Dean had to work three jobs just to make ends meet. Ultimately, Dean and Lindsay didn't inspire each other to grow and evolve.