Movie about man working in department store

So the guy is aimless, he works at a department store at the mall(Sears, Macy’s type). There is a part where he is training a new employee.
He has a girlfriend that visits him from Manhattan. She wants to settle down. He ends up kissing his next door neighbor who ends up graduating high school near the end of the film.
He lives with his brother I recall.

Dont recall where the film is located maybe Up state Ny CT or NJ.

maybe released in 2000 or 2001?