Gilmore Girls: 5 Times Fans Felt Bad For Christopher (& 5 He Was The Worst)

Christopher Hayden is a study in contrasts on Gilmore Girls. While he doesn’t love the wealthy world that he comes from, he seems stuck and unsure about how to break away from it, and he seems both rebellious and somewhat conservative. Viewers know that he loves Rory, but he wasn’t the greatest parent, never establishing a clear connection with his daughter.

While the majority of Gilmore Girls fans always knew that Luke and Lorelai were meant to be, Christopher still played a huge role in Lorelai and Rory’s life. Sometimes fans could offer Chris some sympathy, but at other moments on the series, he proved himself to be immature and unfair.

10 Felt Bad: He Wanted To Know Rory Better

In the season 1 episode ‘Christopher Returns,’ Rory’s dad arrived in Stars Hollow on a motorcycle, and fans were intrigued by this character who they had only heard about before that moment. Christopher wanted to spend more time with Rory, and Lorelai was supportive but felt a bit awkward thanks to their history.

Fans sympathized with Christopher in this situation since he had good intentions and wanted to be in Rory’s life. It soon became clear that his job situation was often in flux and that he was unreliable. But he did seem like he was trying, and viewers hoped for Rory’s sake that he was for real this time.

9 The Worst: He Told Luke He Should Be With Lorelai

In the season 5 episode ‘Wedding Bell Blues,’ Christopher told Luke that he was Lorelai’s one true love and soulmate. This was not only painful for Luke to hear but also the worst timing since they were at Emily and Richard’s vow renewal.

This Gilmore Girls event had heartwarming and intense moments, and this one sticks out to fans, as Christopher was definitely in the wrong. He shouldn’t have said anything at all and he should have stayed out of Lorelai’s romantic life, as it was clear from their dramatic history that if they were going to be together, it would have happened by then.

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8 Felt Bad: Lorelai Turned Down His Proposal

Christopher’s trip to Stars Hollow in season 1 also featured a huge moment for the two characters: Christopher asking Lorelai to marry him. She said no, realizing that he was still immature and figuring it all out. She didn’t want to be with someone who wasn’t on her level, as she had been raising Rory and working hard for years.

Even though many fans ship Lorelai and Luke, it was still heartbreaking watching Lorelai reject Christopher. He had been holding onto the possibility of them getting back together for years, and it was hard for him to let that romantic dream go.

7 The Worst: His Relationship With Sherry Made No Sense

Sherry was introduced in season 2 of Gilmore Girls and Lorelai was definitely surprised to learn that Christopher was dating someone and moving to Boston.

Nothing about Chris and Sherry’s romance felt natural or right. They didn’t seem to get along well and when Lorelai and Rory attended her baby shower in the season 3 episode ‘Take the Deviled Eggs…’ they felt that Sherry was too uptight for him. Fans couldn’t understand what they saw in each other or why they had a child together, only for Sherry to abandon them both and move to Paris.

6 Felt Bad: He Realized Lorelai Loved Luke More

The season 7 episode ‘To Whom It May Concern’ marked the end of Lorelai and Christopher’s relationship. After realizing that Lorelai wrote a letter so she could be a character reference in Luke’s custody case, Christopher knew the harsh truth about Lorelai’s feelings.

The debate over whether Lorelai should be with Luke or Christopher was always present on the show, and this was a huge moment for those who shipped Luke and Lorelai. Fans did feel badly for Chris here since he couldn’t help his feelings for Lorelai, and no one wants to get their heart horribly broken.

5 The Worst: He Talked To Rory About Lorelai Raising Her Alone

In A Year In The Life, Rory and Christopher had a conversation about why Lorelai raised her by herself. Rory wanted to know more about their family story for the memoir that she was writing, but it was also clear that she was finally up to the challenge of asking him this question.

Christopher’s response was that Lorelai wanted it to be that way, so he went along with it. It’s tough to think that this was the right answer. Didn’t he want to be more involved? Didn’t he miss Rory? Fans realized in this moment that while Christopher had his positive qualities, he always stayed a kid and wasn’t capable of parenting Rory.

4 Felt Bad: His Family Pressured Him

Lorelai and Christopher were both shocked to learn that they were expecting a baby in high school. Both sets of parents felt marriage was the right move, but they weren’t ready for that. Over the seasons, fans saw glimpses of Christopher’s mom and dad, and the Haydens were always super strict, rigid, and mean.

Fans felt badly for Christopher as his family put a lot of pressure on him to succeed. While he did have a problem with motivation and following through on business ideas, everyone deserves family love and support.

3 The Worst: He Was Overwhelmed By Gigi

When Christopher had a hard time raising his little girl Gigi, Lorelai stepped in, and they even took her to Paris in the season 7 episode ‘French Twist.’

When fans saw Chris with his child, they couldn’t support him, as she was poorly behaved and he felt totally overwhelmed and stressed out by parenthood. This was another example of how immature he can be, and this was yet another time when he wasn’t ready to be an adult and relied on someone else to help him. Christopher’s refusal to grow up is just one reason why Lorelai and Christopher ultimately divorced.

2 Felt Bad: All His Relationships Failed

Christophe’s romantic situation is one of the saddest parts of his life. He tried so hard to get Lorelai to see that they belonged together, but ultimately, that wasn’t to be. He got engaged to Sherry and she left him with their daughter.

Some could argue that this character picked the wrong romantic partner and that’s why he ended up in this situation, but he was genuinely trying to move on from Lorelai and start fresh, so no one could really blame him for getting engaged to Sherry. Chris was trying to do the right thing here.

1 The Worst: Chris And Lorelai’s Marriage Was A Mistake

Fans have mixed feelings about season 7 of Gilmore Girls, and for many, the worst part was watching Christopher and Lorelai get married. They weren’t right together, and it was clear that they were trying to make something work that was already broken.

Viewers didn’t like Christopher much in this season. He was an obstacle on Lorelai’s path to getting back together with Luke, and he needed to find his own way in the world. If he had been honest with himself, he would have realized that their relationship was over before it even started, so fans couldn’t offer him sympathy here.

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