"W" is missing in "always"
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If it took place the years he was with Christine, then it would've meant he had cheated, and Tori didn't mention him being in a relationship when she brought up their hook-up.
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Did Jason and Christine stay together throughout '91 to '97 without any breaks? His dalliance with Tori was supposedly a summer fling. The fact that Donna and Brandon share that odd Valentine's Day telethon mega-kiss in late S5 has to be a hint re: the time window.
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Well, if they all occasionally hooked up with each other like Tori or 90210 movie suggest, then they all cheated on their partners. It is quite possible Jason did that too, and Tori is not a person who would take care of someone's privacy, so she just spilled it out. That could be one of the reasons he did not want to comment on it. On the other hand, I am not even sure she really had something either with him or Brian. And if she had, I don't think it was really "a thing."
Now, who told me Jason and Tiffani dated? You, Rachel?
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This is quite the thought, lol.
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Long shot, I know, but I somehow could see it happening.