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There's a clock on the top of the screen saying what day it is and what hour.

Well, i think it only show Daylight or Night as the type of days, it does not really help when it comes to Evening, so what time period counts as Evening for the Friday Evening event?

(+1)

About 16:00

Ok, i hope it can be repeated next Friday on that game and not a one time use after asking him about the hunt, otherwise, i might have missed it, and i still have not seen the Caravan scene at the area where you randomly find the male or female bandit in yet, i think i miss my chance to get it now.

The scene with Bernard is not one time event. It's happening every Friday.

Ok, at least i don't have to miss it, does it start in the same place in wherever Caleb is in? Also, is the Caravan event a one time event as well since i keep missing it?

Yes, it's always in the hut in the forest.
Caravan event is not one time even either.

Ok, so it is where i found the Werewolf, i do have a save file in there, so i think i can get it now if i load that one, and ok, when does the caravan appear if it does not appear randomly, but at a certain time in this game?

(+1)

Another question, what happens if Bernard like's me at 100?