Plot hole: When Dawson and Eve are in the PSAT room after hours looking for the test, there is a noticeably open outside window behind them implying that was how they broke into the room. But when the security guard suddenly comes in the room and walks by the window twice, he makes no attempt to close the window and secure the room, which one would think was his job.
Plot hole: When Dawson suddenly shows up at Joey's workplace, Joey is inside asleep at the desk and Pacey is awake sitting outside. As Pacey and Dawson start fighting verbally, their voices escalate loudly but Joey still doesn't wake up even though she's sitting right inside. It isn't until they start throwing punches at each other and fighting physically that Joey suddenly comes running out to see what is going on. It doesn't seem realistic that Joey would be able to sleep through their loud arguing, and not wake up until they are hitting each other. If she had woken up before that, she would have definitely come outside to see what Dawson and Pacey were up to.
Plot hole: When Dawson and Eve are in the PSAT room after hours, looking for the test, a security guard suddenly comes in. They both have time to duck under a desk and avoid being seen, but as soon as the guard passes them, they start talking in rather loud whispers. The guard is still very close to them, as he quickly returns to walk past them going the other way. It seems reckless for them to be talking like that with the security guard so close at hand who would normally hear them, and so soon after he walks by them.