There's an old Japanese movie called "Farewell to Dream" that makes this an art form.
Meet Yoichi! He's a happy teenage boy! He has a best friend, a precocious crush on a neighbor, a beloved sister, and a loving family of shopkeepers. All he wants is to grow up and become a fisherman. Yay Yoichi!
Except oh shit his sister just got sent away to take care of an ill uncle. Ok well that's fine we still have our best friend who's… dad is moving and is leaving town. Well at least he can look out his window at his crush who… is walking outside… heading off to move away and get married. And then his dad dies and his sick mom can't run the business so he has to drop out of school and run it himself. The movie makes it absolutely sure he can never become a fish man. His hopes and dreams broke up with him.