How I Met Your Mother: 10 Worst Breakups

This story about true love was often punctuated with lessons and heartbreaks.

Marshall Lily Breakup

"Kids, I'm going to tell you a story."

A simple sentence that launched a cultural juggernaut for CBS, How I Met Your Mother was the story of Ted Mosby telling his kids the story of how he...well, met their mother.

Featuring a talented main cast that had the sort of chemistry that network executives can only dream of, what originally was dismissed as a "Friends" clone went on to spawn nine seasons, five official tie-in books, and multiple catch phrases that have gained permanent entry into the pop culture lexicon.

With sharp writing and the aforementioned way the cast played off of each other, viewers quickly became invested in Ted's search for "The One".

Along the way, the lives and relationships of Marshall, Lily, Robin, and Barney were also explored and mined for comedic (and oftentimes dramatic) material.

While the premise of the show never faltered from being about Ted and precisely how he arrived in the year 2030 talking to his children, the pitfalls of failed relationships and incompatibility were the crux of the show's run, making Ted's eventual happiness with The Mother that much more rewarding.

With realistic characters and the longevity of the series, the emotional investment in the relationships of HIMYM was very real. Hence when two characters broke up, it resonated with fans. Maybe that explains why the following breakups hurt so much.

10. Ted And Natalie

Marshall Lily Breakup

"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.


Chris is a Canadian now living in Melbourne. He is a connoisseur of fine maple syrups and apologizing. He spent his time preparing to live in Australia by drinking Fosters, only to discover there really is no Fosters over here. There are tons of snakes though. Should have really focused on the snakes instead.