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How do I get the two Dino’s to do each other?

Fail the chase at the end with Hercules.

How would I go about unlocking ‘Countless Lovers’? Is that a fail scene?

I have a bug where right after finishing Pine Island, whenever I try to go up at the four way intersection (with the jail on the left), it gives me a black screen. The music still plays, and I can access the menus, but there's nothing on screen. I had to reload from much earlier in the game and now have to play until that point again. How to I fix/avoid the glitch from happening if it happens again? I don't care about progressing if it's the end point of the build, I just want to be able to go back to earlier locations.