I didn’t quite understand your question, so I’ll work with a lot of assumptions.
There’s two options here that I can think of.
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You’re progressing the main story and you reached a point where you have to ask Jessica for information about the ORG, but she refuses. In that case, you need to raise her love level by progressing her story (Check her card on the heart icon)
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You raised Jessica’s love level to 3 and can’t get it to 4 because it asks you to investigate the ORG. In that case, you need to progress the main story leads. You get them by taking a train to the mountains, talking to Gramps, completing the training and finding the pigeon in the lake. To progress you follow the leads (mail shaped icon)