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There were things that singled a wrench was coming. Logan was having issues with his father but instead of talking with Rory he invited Colin and Finn over. Then he did talk about it but he decided the best way to deal was to go away for the weekend to forget about it.
And Rory didn't tell Logan about her birthday and what it meant. He had to coax it out of her and she still didn't want to talk about it. She just wanted to let the birthday and everything pass.
And Logan was feeling a cooling from Richard&Emily because they found out Rory was having sex. And of course, they found out that what Lorelai said about Logan's family was correct. And Rory wasn't dealing with it either.
The thing was small and should have been easy to overcome. But that was why Jess was brought back. His presence made the situation explode. Imo he was used in the same manner as Christopher. Rory&Logan needed conflict, bring Jess in. He will always be someone they can bring in to cause conflict/chaos.
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