10 Most Heartbreaking Futurama Moments

Thanks to displaced chronotrons the team had harvested to accelerate the growth of atomic supermen to beat the intergallactic Globetrotters at a basketball match (Futurama always was that kind of show), the universe is suffering time skips. Fry and Leela leap from their usual overzealous/disinterested dynamic to being married, though neither has any memory of how it happens. Because of this, they quickly divorce and Fry's dreams are snatched away from him.

That's not where the heartbreak ends though. Just as the crew are sent to detonate an implosion, Leela decides to let Fry fly the ship. She knows he's been practising, and wants to still be friends. If only she'd stayed in the pilot's chair...

Fry is the only one who sees the reason Leela married him. During the time skip, he'd moved the stars themselves to write her a love note in the sky. The implosion destroys it, but Fry excitedly asks if she saw it. When he realises she didn't, he decides not to tell her. The hardest part to take is not knowing if he didn't think he'd be believed, or just thought that after the divorce Leela had made it clear she was happier without him.