Plot hole: When Jen and Jack are talking at the B&B, he picks up the bottle of pills from Jen's purse and asks her about them. She lies, telling him they are pills for Grams when in reality they are Jen's medication. But Jack is examining the label closely, and wouldn't he see pretty easily that Jen's name was listed instead of Grams? He had plenty of time to read the entire label.
Plot hole: Dawson is in his bedroom, and hears a noise outside his window. He panics, and picks up his laptop to use as a 'weapon' if necessary, while approaching the window. This doesn't seem logical; because for one thing he knows Joey is in town and she has been coming in through that window for years, and wouldn't he think of that first? Also-highly unlikely Dawson would actually use a very expensive Apple laptop as a weapon when it could be damaged, and he relies on it extensively for his work as a Writer/Producer.