How I Met Your Mother: 10 Worst Breakups

10. Ted And Natalie

"New is always better."

One of Barney's many rules, first mentioned in season eight in regards to the choice between a fresh romantic partner or someone who history has already been had with.

Of course, with Barney serving as the id to Ted's everyman, it would make sense that the hopeless romantic would stray away from such a mantra. Indeed, throughout the course of the show, Ted finds himself drawn back to past relationships on more than one occasion.

The earliest example of this pattern occurs in just the fourth episode of the first season, when Ted discovers a shirt in his closet he used to hate, but now finds he quite enjoys the look of. It then stands to reason that this change of heart can also be applied to an old flame that didn't seem a good fit at the time, right?

Enter Natalie, Ted's former girlfriend whom he broke up with via answering machine on her birthday. Naturally, courtship the second time around takes a bit of convincing, but Natalie and Ted eventually begin to date again and everything seems terrific...for about five minutes.

Ted realises that he had it right the FIRST time, and Natalie still isn't the right fit for him. Unfortunately, history repeats itself and Ted finds himself breaking up with her on her birthday once again!

Sure, it's played for laughs, but when Natalie says "You've given me the best gift of all. How to trust again" right before Ted breaks the news, it's absolutely devastating. Thank goodness for the laugh track.