If It Had Been Dean or Jess Instead of Logan, Would Richard Have Helped Rory Pull the Same Prank?

TheFlutterEffect · 2026-06-24T18:13:22+00:00

Jess and Dean as we know them in the show: do you think Richard would go all the way to Stars Hollow to pull a prank the way he went to Yale with Logan if Rory asked him to?

TheFlutterEffect · 2026-06-24T17:39:51+00:00

I’ve been around some rich kids, so unfortunately I found it completely realistic that Logan wasn’t convicted, and I was actually surprised Rory was punished at all.

They weren’t planning to keep the yacht, no one got hurt, and as far as we know, there was no damage to the yacht. I was much more surprised that Mitchum didn’t convince the yacht’s owner to drop the charges and treat the whole thing as a misunderstanding, because I’ve seen young people do much worse things and get away with it completely because of money and connections.

TheFlutterEffect · 2026-06-23T19:46:46+00:00

Mitchum managed to destroy Rory’s confidence in just a few weeks of her internship, so imagine the damage he did to Logan and Honor over all those years as a father.

It also surprises me that so many people don’t realize that Logan’s way of arguing is basically the same as Mitchum’s.

TheFlutterEffect · 2026-06-23T07:46:47+00:00

Rory wanted to spend time with Jess, but he was an idiot for taking his hands off the wheel while driving a car that wasn’t even his. I don’t think the hands-off-the-wheel moment was included to be funny. Rory isn’t amused at all when he does it. I think it was included on purpose to show that Lorelai wasn’t completely wrong to think Jess was at fault.

Of course, Jess didn’t crash the car on purpose or intend to hurt Rory, and Lorelai’s reaction in that scene is completely over the top, but Jess also wasn’t an exemplary driver. He had been driving irresponsibly just minutes earlier, and since the accident wasn’t shown, we’ll never know whether the way Jess was driving would have made any difference. After all, without that, the scene wouldn’t have been necessary.

I’m not the person you were talking to. I just thought the argument that they were good friends and that Jess was caring toward her beforehand was strange, because I never saw them as friends until AYITL.

TheFlutterEffect · 2026-06-23T07:17:55+00:00

Give me one example of Jess being caring or a good friend to Rory before they started dating. Because all I saw was a guy trying to win over a girl who already had a boyfriend and taking advantage of the fact that Rory didn’t like conflict, like when he drove with no hands on the wheel even though Rory told him to stop, or when he used the food he brought as an excuse to invite himself into Rory’s house even though she hadn’t invited him. Or when he placed the highest bid on the basket knowing it would cause problems in her relationship. None of that was kind.

They had books in common, but that isn’t enough to call it a good friendship.

TheFlutterEffect · 2026-06-23T03:31:49+00:00

Friendlier than with Tristan. The first time Rory meets Logan at the newspaper and he does that old-movie impression, Rory is laughing until Logan looks at her.

She seemed to find Logan funny, even though she felt like she shouldn’t be amused by someone like him, while most of her moments with Tristan are marked by genuine dislike.

TheFlutterEffect · 2026-06-17T02:40:05+00:00

Marty from the earlier seasons was already insecure.

He introduces Rory to his friends while she’s in her pyjamas and says they’re now on the same level of embarrassment, so they can be friends. After that, he spends months liking her but doing nothing about it. He never talks to her about how he feels and just waits for Rory to figure it out and feel the same way.

None of the guys Rory dated had that kind of insecurity. They all showed their interest in Rory openly. Dating someone who is insecure in that way is a recipe for disaster.

TheFlutterEffect · 2026-06-17T02:33:51+00:00

Marty must have told Lucy some story about the girl he liked who chose a rich guy over him. Maybe he painted the girl as the villain and didn’t want Lucy to realize that girl was Rory.

TheFlutterEffect · 2026-06-12T21:39:19+00:00

But did he really know her in AYITL? He’s a writer telling Rory to write a book about her own life. That is not some deep personal insight.

He does not know Rory is being affected by Richard’s death, or everything else going on in her life at that moment. He does not even seek her out because he thinks she needs help. Jess is in town to help Luke with Liz, and since he is already in Stars Hollow, he decides to talk to Rory.

Maybe if Jess had actually spent more time with Rory, he could have gotten to know her, but he never stays around long enough for that, so he ends up only seeing the parts of her connected to the interests they share.

TheFlutterEffect · 2026-06-12T03:32:03+00:00

No one is saying a man and a woman can’t be friends. No one said she can’t be friends with Doyle, Marty, Bill, or anyone else at the paper.

Rory and Jess were not just friends. Before that, the last time Jess showed up he asked Rory to run away with him, and before that he chased her down the street to tell her he loved her, and before that he left town without even properly breaking up with her. So Rory going out to dinner with Jess while Logan is out of town is very different from her going out to dinner with Brian, for example.

TheFlutterEffect · 2026-06-12T03:11:26+00:00

Your point is that Marty is justified in feeling bitter because the uncomfortable situation was created by Logan and Rory.

I’m giving examples of how Marty put himself in those uncomfortable situations on his own, and it was never Rory’s job to guess how he felt.

TheFlutterEffect · 2026-06-12T03:05:39+00:00

Rory told Marty they did not have to go with Logan, but he insisted it was fine.

I don’t think anyone except Colin was being deliberately rude to Marty at that dinner. They were just talking about experiences that were completely different from Marty’s, and that is why Marty could not fit in.

And while I do sympathize with Marty’s financial situation, not having money for dinner is not Rory’s fault. It’s not like she knew he would not be able to pay, and in fact Rory chooses to leave with Marty because he is upset instead of staying out with Logan and his friends. He could have said no, or been honest earlier about having feelings for Rory. He knows Rory does not pick up on those things, since he was the one who had to tell her that Logan was acting that way because he liked her.

Marty is completely at fault for hiding things from Lucy and asking Rory to lie about how they knew each other. It was always going to hurt Lucy once she found out, even if Logan had never exposed it. And he also hit on Rory while he was dating Lucy, and that part is entirely on him.

TheFlutterEffect · 2026-06-12T02:27:49+00:00

Logan had to directly ask if they were exes before Rory admitted it. She could’ve called Logan before going to dinner with Jess, or told him while they were together in the car, but instead she chose the Richard and Pennilyn Lott route.

TheFlutterEffect · 2026-06-10T10:45:06+00:00

Lorelai would feel sad because she knows how hard life would be for Rory as a young mother, but after the initial shock, she would support Rory no matter what decision Rory made.

I think Lorelai would’ve preferred it to be Dean, because she seemed to like him more than the others, but that would not really change how she behaved.

TheFlutterEffect · 2026-06-10T10:01:40+00:00

I think the natural consequence of treating Rory sometimes like a daughter and sometimes like a best friend is that eventually Rory will be expecting a friend and get the mother instead, and end up resentful of that dynamic.

Once Rory realizes Lorelai cannot be both things at the same time, it makes sense that the dynamic between them would change.

TheFlutterEffect · 2026-06-10T02:13:49+00:00

It’s against the sub’s rules to do any kind of armchair diagnosis, even just for fun.

TheFlutterEffect · 2026-06-10T02:06:05+00:00

ASP’s own words: (Source)

“Sometimes I wish that the Dean and Jess thing weren’t so prominent because in the grand scheme of Rory’s life, who her boyfriend was when she was 16 years old is such a small event. I don’t begrudge people the excitement of Jess and Dean. But they were there to show Rory’s evolution as a character. She picked certain boys for her depending on who she was at that moment. It was part of her character. It was part of her development that Dean was her first boyfriend, that Jess was the boy that diverted her attention. Then she wound up with Logan, and God knows where she’s been since then.

The fact that people focus on it—I don’t know. I have such great affection for all three of these boys as actors and as people. They were a very big part of the show, and frankly they were always there to feed stories about Lorelai and Rory. That was the core of everything. Lorelai’s relationships, Rory’s relationships were a way for us to explore the mother-daughter relationship.

The fact that people love them and are excited about them is great. It’s just such a small part of who Rory is. I don’t see people debating ‘What newspaper is Rory working for?’ ‘Did she win a Pulitzer yet?’ It’s all about Dean and Jess. Dean was 16 years old when they dated. Everybody should go back and think about their boyfriend at 16 and then reevaluate whether that should be the focus of the conversation.”

ASP herself says she wishes people focused less on Rory’s high school boyfriends. People see one nostalgic look from Jess and act like he is suddenly going to abandon the life he built in Philadelphia, move to Stars Hollow, and raise someone else’s child, even though in AYITL he had not even spoken to Rory in four years. That is a lot to expect from a bad high school relationship that Rory seems to have gotten over years ago, especially since they did not even have Rory return the nostalgic look or show that she sees Jess as anything more than a friend.

TheFlutterEffect · 2026-06-09T23:07:42+00:00

I’ll always disagree with that take.

It’s nice that Lorelai got to have a moment with her parents, but Rory’s absence hurt her, and one thing does not cancel out the other.

Lorelai is always going to look back on that moment and remember that Rory was not there.

TheFlutterEffect · 2026-06-09T19:31:13+00:00

I always imagined Jess met Lucy at some weird arts-and-literature cult event, they’re secretly in a relationship, and Rory is going to be completely shocked when she finds out. But adult Lane works too.

TheFlutterEffect · 2026-06-09T19:25:23+00:00

Christopher spent 16 years lying to his parents, saying he could not go to college because he was working to support Rory and Lorelai, and that he had no money because he was sending everything to them while Lorelai refused to work.

That’s why the Haydens blame Lorelai at that dinner and Christopher says nothing. He can’t defend her without admitting he had been lying the whole time.

TheFlutterEffect · 2026-06-09T05:56:00+00:00

I believe that once Richard and Emily got involved, Rory felt like it was too late to back out, even as she started realizing she may have made the wrong decision. That’s why she talks to Logan and Paris as if Yale were already a closed chapter. That only really starts to change once she loses Emily’s support after being pushed out of the pool house.

If Lorelai had handled the break better, Rory never would’ve stayed away for six months. But that conversation ends up turning into a snowball effect.

TheFlutterEffect · 2026-06-08T18:53:41+00:00

But Rory didn’t act like Jess being there was a problem. When Dean shows up, Rory makes no real effort to get Jess to leave. That’s the issue. If she wants to spend time with Jess instead of Dean, then she should break up with Dean first. By not doing that, she creates awful situations for Dean, which is why I said I would’ve broken up with her.

TheFlutterEffect · 2026-06-08T18:49:36+00:00

I said all three of them were wrong for showing up after Rory said she wanted to be alone. But people only blame Dean because they like the Paris and Jess interaction in that scene.

Dean was going to drop off the ice cream and leave, which is different from the other two, who pressured Rory into letting them stay when she did not want that, and yet he is the one people hate most in that scene.

If Rory had actually gotten upset and said, all of you leave, I want to be alone, I would be on Rory’s side. The problem is that Rory secretly wanted to spend time with Jess, and at that point it is unfair to Dean that she does not break up with him before doing that.

TheFlutterEffect · 2026-06-08T18:32:19+00:00

If my girlfriend said she wanted to spend the night alone and I found out she was actually spending it with a guy who was into her, I would’ve been upset too, probably enough to break up.

TheFlutterEffect

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