Damon Salvatore - The Vampire Diaries
Damon's love for Elena may have been obvious, but he had never actually said it out loud. In a moment of selflessness, Damon tells Elena he loves her before erasing her memories. He confesses that he doesn't feel worthy of her love in return.
Josh - Younger
No matter what she did to him, Josh couldn't stop going back to Liza. He was even about to call off his wedding so he could return to her once more. But at the end of the day, Josh realized he had to let Liza go for his own sake and the only way to do that was to put a ring between them.
Michael Guerin - Roswell, New Mexico
The Roswell season finale was heartbreaking for more reasons than one. After confessing to Isobel that he would always love Alex, Max decided to be with Maria since his relationship with her was less complicated.
Ben Pownall and Maddie Bishop - Siren
Being in love with a mermaid isn't easy. Ben and Maddie constantly have to let Ryn go back to the water, and each time they're not sure if they're going to see her again.
Alexis Rose - Schitt's Creek
Alexis letting go of Ted and putting his happiness above her own is a huge testimony to how much her character has evolved. We didn't see it coming, but we're proud of Alexis for her selfless decision.
Justin and Alex Russo - Wizards of Waverly Place
We may have to go back to our childhood for this one, but the Russo siblings need to be included on this list. Both Justin and Alex had to let go of their true loves during the show, and they were probably the most heartbreaking moments Disney Channel has ever created.