Jen Lindley, granddaughter of the old lady who lived next door to the Leerys, moved in with her grandmother, and Dawson recruited her to work on the movie. By implication, this also brought her into his circle of friends. She proved to be a natural at everything, including keeping Joey and Pacey in check. The film wound up winning first prize at the Boston Junior Film Festival. The prize included a sum of money, to be put towards his next project. Dawson of course recruited Jen to be his producer.

The subject of the story for his next film, was somewhat autobiographical, and this annoyed Joey, with whom he had recently gone out with, and the relationship had ended badly. This of course lead to a rather intense argument, which was eventually resolved, and she continued to work on the film, and it proved to be a great success, until Dawson's high school film teacher rubbished it.

Dawson was not perturbed however, and pushed on. His next piece was a documentary, about a mysterious place called Witch Island. This of course drew inevitable comparisons to The Blair Witch Project, which had only just come out. Everything seemed to be going well, until a festival screening, which had left the audience apathetic and underwhelmed. Dawson began to wonder if maybe film-making wasn't for him after all. However, he met another filmmaker at the festival; a girl by the name of Nikki. She was able to give him some advice and constructive criticism, one filmmaker to another, which prompted him to return the favour.

It turned out Nikki was the daughter of Dawson's High School Principal, and she briefly followed him back to Capeside. However, Nikki's father would be fired under controversial circumstances (i.e. for being black), and Dawson eventually stitched together some news footage, and some interviews with Nikki to put together a documentary about the events. This had a much different audience reaction at the festival where it was shown.

During Dawson's senior year of high school, when he was considering where to go to college, he came to know a curmudgeonly old man by the name of Arthur Brooks. While sorting through the old man's archives (at his request), he discovered Brooks had been a somewhat successful director in years gone by. Dawson eventually got him to open up about his career, and why he had stopped making pictures (as Brooks called them). Dawson eventually used this as the basis of his next project; a documentary about the life and career of Arthur Brooks. Unfortunately, Brooks, who was quite old, would not live to see the finished product. However, this experience helped Dawson rediscover his love of film-making.

Dawson would eventually be accepted into USC Film School's summer program. If it went well, it would likely lead to him being accepted into an undergraduate program. But this would mean he would have to leave Capeside, and his friends (who were all accepting into colleges in Boston). Especially Joey. He knew he would miss Joey, and she would miss him. After spending his last full day in Capeside with all his friends (much to his father's annoyance), he once again found himself in his bedroom, with Joey, like thousands of other nights. But this was different. This would be their last night together for some time. After she helped him pack, they said their goodbyes, and Joey confessed she didn't want Dawson to go. Dawson explained that it was time for them to move on with their lives, and onto bigger and better things.

Then they kissed, and fell asleep in each others arms. He woke up early the next day, careful not to wake Joey. He showered, got dressed, and carefully picked up his suitcase, walked slowly and quietly down the stairs, to the taxi waiting outside. The taxi took him to the Airport, which took him to Los Angeles, where his new life would be waiting for him. He considered calling Joey from the Airport, or after he had landed, but thought it would be better to make a clean break from her and his old life, at least for now. But this would prove to be a big mistake, one which threatened to send his (new) life crashing down around him...