Dawson: How can you be friends with someone when every time you see them you think about how much more you really want?
In the opening scene when Joey and Pacey are returning to Capeside on Pacey's boat, they had to shoot the scene 3 times because the boat was rocking too much. Production finally sent to LA for a special "Steady Cam" sort of rig, and it finally worked on the 3rd shoot. See more...
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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.
Continuity: When Andie is doing sit-ups in the morning and practicing for the PSAT, she is listening to the news on TV. The news anchor mentions the author of the popular book "Cracking the PSAT". She says 'PSAT' not 'SAT'. But Andie immediately says something like "Way ahead of you", and holds up her copy of the book. On the cover, it says "Cracking the SAT", not 'PSAT'.
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.
Continuity: Right after Pacey leaves Dawson's bedroom at the beginning of the episode, Dawson looks out his side window to see Pacey leave and suddenly notices flashlights in the dark house next door. It's clear that Dawson is looking out the side window on the right of his bed, as he is directly facing Jen's house. There is also a side window to the left of his bed which also faces the same direction. But in a later episode (Guess Who's Coming To Dinner); they show a wide shot of that side of Dawson's house. There are two windows on that side of his house facing Jen's house, but they are on each side of a chimney and the two windows make up the complete upstairs (looks more like two rooms). But whenever we see Dawson's bedroom, it's much smaller and does not take up the complete upstairs space of the house. In fact, there is a clear upstairs stair landing that his bedroom is off of, and this landing looks out over a large open space with the dining room, living room, etc. So there is no way that Dawson's room with both side windows could possibly take up the entire sideways width of the upstairs as is shown from the outside. There is also no fireplace and chimney that runs the entire height of the house on that side of the house, and which would in theory be located right where Dawson's bed is between his two side windows. Obviously the real house exteriors differ considerably from the inside sets.
Plot hole: When Dawson picks up the phone in his bedroom after seeing the lights in the house next door, he dials 9-1-1 (You can hear the three beeps from the phone buttons). Yet when the person on the other end answers the phone, she says "Capeside Police". Later in the episode Doug also makes a reference to Dawson dialing 911. Yet when he called 911, they should have responded "911" instead of "Capeside Police". Normally when you call 911 you would get a 911 operator, not be put directly through to the local Police until you requested it.
Continuity: When Jack and Andie are using the computer with Ben's Instant Message on the screen, there is a close-up of the computer screen as they wait for Ben's photo to download. Just to the right of the photo is the entire IM, which shows all 3 lines of dialogue between Ben and Jack. The last line says, "So. What do you think?" But after the photo is finished, there is a sudden 'beep' from the computer signalling another incoming IM message, which Jack then reads out loud as if it is a new message. But what he reads is, "So. What do you think?", the exact same line that was already in the IM box before the photo finished downloading. The implication is that he is reading a message that just came in, yet that line of dialogue from Ben was already present in the IM box previously.
Plot hole: When Jen is helping Dawson at the Video Store, and spots Pacey and Joey out on the street, she asks, "Dawson, do you have one of those little signs that says 'Back in 5'?" Dawson then relies "Yeah", implying he could leave the store for several minutes on a small break. But then he and Jen follow to where Joey and Pacey are taking their dance lesson. Dawson then proceeds to dance his way through an entire dance lesson, witness a confrontational scene in the coat closet, and then lingers outside in the street having a meaningful conversation with Joey. This would all obviously take up a considerable amount of time, much more than a small break. Therefore - how would he have gotten away with closing down the Video Store for that amount of time without losing business and possibly his job? Especially if the sign only indicated he would be away a few minutes. This would be very un-Dawson-like to be that irresponsible with his only place of employment.
Plot hole: When Jack and Andie are using the computer at school, Jack shows a clear knowledge of computers by explaining search engine criteria to Andie. It's also mentioned that they had already done an extensive background check on Ben, again implying that Jack has extensive computer skills. So why would Jack, who is apparently quite skilled with computers: not know what an Instant Message is, not know how to 'get rid of this thing' by clicking off the IM window, and not know to click 'Send' in order to send an IM back to Ben. It doesn't make sense that Jack would know so much about computers, and not have any awareness of how something as simple and basic in Internet usage as 'Instant Messages' would work.