How I Met Your Mother: 10 Worst Breakups
2. Ted And Robin
In a clever last minute reveal during the pilot episode, it was firmly established that Robin is NOT the mother of Ted's kids.
Still, that didn't stop the majority of the first season centring around Ted's pursuit of Robin as a romantic interest. He is successful after (questionably) making it rain as a sign the two should be together, and the two spend the entirety of season two as a couple.
It's interesting that the show played its hand so early, as it adds a countdown dynamic to the relationship since it's been established things will not last. In fact, Ted echoes this sentiment in the season two finale when he says to Robin "We have an expiration date, don't we?"
None of this changes just how hard it is to sit through the couple slowly coming to the realisation that they aren't meant to be together. This relationship doesn't end from a falling out, or due to dysfunction. Quite the opposite; Ted and Robin are a great couple, but a couple that is great in the present that has no long term future.
The mutual decision to end it, punctuated with Ted's line "I would have stolen you a whole orchestra" triggers tears no matter after how many viewings.