- „Here's some for you. Don't give up. True love always wins in the end”
- —Will to Pacey[src]
Will is a very contemplative, quiet and kind person, who's very caring and supportive to his friends, helping out and offering advice. He deals with a lot of anger towards his father, who doesn't understand Will and also treats Will's mother badly. Getting into Rawley is sort of an escape for Will, who grew up locally and spent a lot of time dreaming of opportunities to explore the world.
Will is first introduced when visiting Pacey for a few days in Season 3. Joey, Pacey and Dawson all knew him when they were kids, and he is invited along on their spring break trip to Dawson's Aunt Gwen's house. During the trip Will gets along with everyone easily, especially he and Andie get along, and eventually develop a romantic interest in one another. Will helps Pacey race in the Capeside Regatta, and supports him, as well as Andie, when everyone finds out about Joey and Pacey.
He is a very good friend to Pacey, recognising Pacey as he is, and not as Pacey's family may perceive him. Pacey later tells Andie that he and Will initially bonded over their bad relationships with their negligent fathers. After Andie finds out about Pacey & Joey, on the evening of her date with Will, he encourages her not to be consumed by anger toward them, saying she wouldn't be the person he has come to know her to be, which inspires her to try and mend things with Pacey.