When things starts to repeat itself and people begin to appear in unexpected places a older man tries to understand what is going on.

This is a great start! I would like to see a clearer event, character and action though.

What starts repeating itself? How is that related to the man?

Who is this man, apart form being old - give him an adjective that is more descriptive of his character.

What does he have to do? Understanding what's going on seems to be the first step, but what he does with that information is the exciting part. Let that be the action of the logline.