So chronologically, Entry #20 took place before Entry #15. In Entry #20 Alex, Tim, and Jay were together. So obviously Jay and Tim met. Yet in Entry #15, they were talking as if they just met for the first time. "uh Jay right?"
Now, I have a theory that Jay encountered the operator prior to even creating the YouTube channel and he made Jay lose his memory. That would explain him not only forgetting Tim but also the events that took place in the entries and forgetting about the tapes themselves.
Now that would explain why Jay forgot about Tim. But do you think Tim also lost his memory? Was he pretending he never met Jay before? If so, why?
I'm thinking maybe Tim lost his memory during the events in Entry #51.