Plot hole: When Jen and Henry are talking in the park, he tells her that he's 15. But later in Season 3, he has a Birthday party at the Skating Rink in which he would have to be turning 16. Henry is a Freshman, and it's highly unlikely he would be turning 16 in his Freshman year. All the main characters of Dawson's Creek turned 16 during their Sophomore years. It also doesn't seem likely that Henry would have skipped an academic school year, as his personality/character doesn't appear to be intellectually motivated.
Plot hole: When Jen and Grams are talking on the porch, Dawson walks up to talk to them. They ask him if their cab has arrived, and he says no, but they are in his shot. They then choose that time to say goodbye to Dawson, which turns into a group 'goodbye' with everyone that lasts several minutes. Meanwhile, the cab has arrived, and when they are finished saying goodbye, Grams, Jack and Jen walk to the cab and get in to leave for NYC. But what happened to all their luggage for the trip? How did it get in the cab? They went straight from saying goodbye, into the cab without stopping to carry their luggage to the car.
Plot hole: During the Leery's Christmas party, Jen asks Jack which colleges he applied to in her name. He replies: Bard, Brown, Columbia, Emerson, Sarah Lawrence, and BU (Boston University). But later in this season, Jen goes to visit NYC because she was accepted into the University of New York. How could she have been accepted there when she never applied? Jack didn't apply for her there, and she didn't fill out any college applications herself.
Plot hole: In the beginning of the episode, Joey and Audrey are talking in their dorm room. Audrey makes a comment that "Our time in this particular room is over". They have been in the same dorm room (27) for two years now, their Freshman and Sophomore years at Worthington. They still have 2 more years to go. What would make Audrey think that they would suddenly have to change dorm rooms when they've had the same room the entire time? Or that they wouldn't still be roommates the next academic year at Worthington? Audrey is staying to take Summer School classes so she doesn't have to leave the University. (00:08:40)
Plot hole: The morning after everyone stayed at the Potter B&B, there is a fun kitchen scene showing all the kids dancing together preparing breakfast. Andie seems to be making pancakes. Yet later at breakfast, Joey finds out that Bodie has come back and is the reason the pancakes taste so good. Apparently he was the chef that morning, but he is nowhere in sight during the breakfast-making scene. So if all the kids are cooking - where is Bodie? Wasn't he supposed to make the pancakes?
Plot hole: When Pacey first finds Emma in the bathroom cleaning the toilet, she makes a point of mentioning that 'she has band practice in an hour'. But right after they 'strike a deal' and Pacey agrees to her terms for the party, Emma suddenly announces that 'she is off to band practice'. Only a few minutes have passed, so it seems strange Emma would suddenly be going to a band practice that doesn't actually start for another hour.
Plot hole: When Dawson goes over to Joey's house to talk to her about Pacey's school problems, he mentions that Pacey had missed that entire day of school. Joey apparently didn't know this, as she is surprised at the news. Since Joey and Pacey are closely involved - wouldn't she have noticed his absence at school that day already? Surely she would have noticed Pacey missing for an entire day of school.
Plot hole: Mrs. Valentine almost fires Joey, after discovering that she lied about knowing the Owens. Drue steps in and saves Joey's job by claiming he did see the Owen boy. But Joey keeps her job throughout the rest of that season. Since the Owens were said to be in Paris only until the 1st of the year - wouldn't Mrs. Valentine have found that Joey lied about knowing them as soon as they returned to Capeside? Surely Mrs. Valentine would have mentioned Joey to the Owens; thinking she was their good friend, and because she was new on staff at the Country Club they were members of the board for. And once she found out Joey had indeed lied, why did she not fire her at that point?
Plot hole: When Chris arrives at the beach house, and invites everyone to the MTV concert a few blocks away; he tells them to follow him there implying that he can get them in free with his 'clout' as a movie star. But later during the first song, Joey and Charlie arrive walking up the stairs from the beach apparently just coming from the beach house. They walk right in to the concert area - no problem. But how would they get in without Chris? They didn't have tickets, and Chris wasn't with them to usher them in. It wasn't likely an event open to the entire general public; as it would be too crowded, and not just the younger people MTV audience for TV.
Plot hole: Dawson and Jen are in a small 'darkroom', developing photos and speaking at a normal level. This darkroom is located just behind the main stairs, and very close to the living room where Dawson's parents are 'getting busy'. Therefore, the parents normally would have heard their voices so close to them, and known they were in the house and not been so surprised by them.
Plot hole: At the end of the episode, Joey takes a taxi from Boston to Eddie's house in Worcestor. As she walks up to the front door, the cab leaves. Eddie has no idea Joey is coming, and she has no way to return to Boston without using a cab or asking Eddie for a ride. But she doesn't even know yet if Eddie is home, and whether he would offer to drive her home. Seems illogical for Joey to dismiss the cab without asking the cab driver to wait a few moments while she sees if Eddie is home, and if he would be willing to drive her back to Boston. Otherwise, she would have to ask his parents to use the phone to call another cab. (00:38:45)
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.
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: Joey tells AJ that her Mother used to read "Little Women" to her, and in fact named her 'Josephine' because "Little Women" was her favorite book. But in a previous episode when Joey and Dawson visit her Mother's grave, the gravestone has printed 'Lillian Josephine Potter', meaning her Mother already had Josephine as her middle name. So naming Joey 'Josephine' wasn't only because of the book "Little Women"; her Mother more likely named her that because it was her middle name.
Plot hole: After Drue has spent the night at Jen's house, Grams explains to Jen that she had a nice talk with Drue right after Jen left for school. But this doesn't make sense, because why would Jen have to be at school a certain time, and Drue not go to school at the same time or at all? His attendance at school would have been required as well.
Plot hole: This scene reveals that Joey has brought Dawson a special gift from her sailing trip with Pacey. It's a brick from the foundation of Ernest Hemingway's home in the Florida Keys, symbolic to 'build the foundation of a friendship' between her and Dawson. In reality, it's highly unlikely that anyone would have allowed Joey to damage a foundation wall by prying out a large-sized brick; and steal it from the premises of a famous, historic home and landmark. (00:36:15)
Plot hole: Dawson and Audrey are planning to fly to LA together, and he already mentioned to Audrey that he needs to stay at her family home for awhile. But then at the end of the episode; Pacey talks Audrey into driving to LA with him, and Dawson is left to fly to LA by himself. Wouldn't this make for a very awkward situation if Dawson flew to LA a few days before Audrey arrived by car, and had to stay with her parents completely by himself having never met them before? Doesn't seem like something Dawson would do.
Plot hole: When Pacey and Joey are unloading the groceries from the car for her party, Pacey makes a remark that he has to go to Joey's garage to get a dolly to haul in the charcoal. But Joey's house doesn't have a garage. During the entire series; there has never been a visible garage on their property, and the large blue truck is always parked out front in the open.
Plot hole: When everyone first shows up at the Airport, it's daytime and not too late. Joey then works an entire shift at the Capeside Yacht Club, probably through the dinner rush until later that night. When Joey and Pacey are talking on the dock after she is through working, it's late at night. They suddenly decide to rush to the Airport where they assume everyone is still waiting for their flights. Being as this must be several hours later since they all met at the Airport, would everyone's flights really be delayed that long? (00:30:05)