Deliberate mistake: Skylar's leaving is edited together with footage of Will sitting in a park watching planes take off - including, presumably, her plane. The sun is directly overhead in his scenes, while hers were filmed near sunset. (Most obvious when you see the very long shadows during the same airport footage which is also used in the deleted scene "Pudge Fisk Card"). (01:39:20)

Good Will Hunting (1997)
1 deliberate mistake - chronological order
Directed by: Gus Van Sant
Starring: Matt Damon, Robin Williams, Ben Affleck, Minnie Driver
Genres: Drama
Continuity mistake: In the construction site scene, you will notice the length of Ben's cigarette fluctuates several times. It actually gets longer/shorter as Ben smokes it.
Will: You know, I was on this plane once. And I'm sittin' there and the captain comes on and he does his whole, "We'll be cruising at 35,000 feet, " then he puts the mic down but he forgets to turn it off. Then he turns to the copilot and goes, "You know, all I could go for right now is a fuckin' blow job and a cup of coffee." So the stewardess fuckin' goes bombin' up from the back of the plane to tell him the mic's still on, and this guy behind me goes, "Hey hun, don't forget the coffee!"
Trivia: Robin Williams won his only Oscar for his performance as Dr. Sean Maguire in this film.





Chosen answer: Will is not wasting his potential. Sean knows that Will has overcome many of his emotional difficulties and with his exceptional abilities, there will be many other job opportunities, regardless of where he lives. Sean believes it is far more important for Will to pursue a lasting relationship with a woman for the first time in his life.
raywest ★
Will had multiple job offers - someone of his intelligence could pick up any job he wanted hence he wasn't disappointed.