How I Met Your Mother: 10 Saddest Moments, Ranked

For a comedy series, How I Met Your Mother made its viewers cry an awful lot. The show felt like a really long romantic comedy, with genuine characters and heartfelt emotions. Just like any romcom, there were ups and downs, with both moments of hilarity and moments of heartache. Friends, a show that How I Met Your Mother is often compared to, had dramatic moments to undercut the comedy, but they were never anywhere near as effective as HIMYM’s most heartbreaking scenes.

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So, in anticipation of your latest re-binge, here are How I Met Your Mother’s 10 saddest moments, Ranked.

10 When Stella left Ted at the altar

Ted Stella HIMYM - Worst TV Weddings

Poor Ted. He just wanted to do the right thing. Stella objected to Ted inviting Robin to their wedding, so he decided to invite Stella’s ex Tony to level the playing field and prove that inviting exes to your wedding is fine. But then Robin decides she shouldn’t be there and takes the ferry back to New York, where she sees Stella and Tony canoodling together.

Ted finds a note and realizes he’s been left at the altar. One by one, his friends join him and try to comfort him. Fans didn’t really like Stella from the off, so no one was disappointed when she left, but we all felt bad for Ted.

9 When Ted realizes he’s alone with one ticket to Robots vs Wrestlers

On the whole, season 8 is one of How I Met Your Mother’s weakest installments, but “The Time Travelers” is a terrific episode... one of the show’s best, perhaps. Ted spends the whole episode arguing with Barney and future versions of themselves over whether or not he should go to Robots vs Wrestlers while Marshall, Lily, and Robin argue over who a drink should be named after.

At the end of the episode, Barney tells him he’s just a figment of his imagination. The Marshall, Lily, and Robin storyline happened months ago. Barney and Robin are planning their wedding, Marshall and Lily are looking after their baby, and Ted is alone with one ticket to Robots vs Wrestlers.

8 When Barney couldn’t forgive his dad

When Barney finally met his biological father, he was disappointed by how lame he’d become. He used to be a roadie who toured the United States with some of the biggest rock bands in the world, sleeping around with more women than Barney himself, but now, he’s settled down into a suburban existence with a wife and kids.

Barney is ostensibly disappointed by this, because his dad isn’t as cool as he thought he was, but then he reveals why he’s really unhappy: “If you were going to be some lame suburban dad, why couldn’t you have been that for me?”

7 When Marshall listened to his dad’s final words to him

In the episode “Last Words,” Marshall spends his dad’s funeral hung up on a voicemail he received from him between the last time he saw his dad and his dad’s death. All throughout the episode, Marshall thinks that his dad’s final words to him were simply a recommendation to watch Crocodile Dundee III.

However, he leaves the church during the service and listens to the final message, a pocket dial that ends with Marshall’s dad saying, “Marshall? Oh, looks like I’ve been calling you for almost five minutes. How’s my pocket sound? Oh, sorry about that, buddy. Um, anyway, your mom and I had such a great time seeing you. I love you.”

6 When Lily opened up about the struggles of parenthood

After Marshall and Lily had a baby, on the surface, it seemed as though they were adapting to parenthood pretty well. But then, in one of the show’s darkest moments, Lily was brutally honest to Ted about how she really feels: “Sometimes I wish I wasn’t a mom.

Sometimes I want to pack a bag and leave in the middle of the night and not come back.” She told him this because it’s her deepest, darkest secret, and she wanted him to reveal his own deepest, darkest secret, so she told him something that was worse than anything he could tell her.

5 When Ted showed us how devastating Robin and Barney’s engagement

When Barney reveals that he’s been orchestrating “The Robin,” the final play in his Playbook, in order to woo Robin and eventually propose to her, Ted gives the engagement his blessing. But then he gets a text confirming the engagement and he describes the emotional agony he felt in that moment to his kids with a fast-cutting montage of every single moment in the series where he got punched, kicked, or otherwise seriously injured.

He then says that it felt like all of that pain combined and then multiplied by a million. We get a pretty clear idea of what he’s talking about.

4 When Ted found a heartbroken Marshall in the rain

The first season of How I Met Your Mother ends with two huge uppings of the stakes. First, Ted and Robin properly get together, so Ted feels on top of the world. Then, he returns home to find Marshall sitting in the rain on the steps outside their apartment building, looking forlorn and holding Lily’s engagement ring.

In a million years, the last thing How I Met Your Mother fans were expecting was for college sweethearts Marshall and Lily – perhaps the most adorable couple in the world – to break up. These final moments of season 1 were still memorable eight seasons later.

3 When Robin shakes her head at Barney

When Barney and Robin are both in relationships – Barney with Nora and Robin with Kevin – they make the worst mistake that anyone in a relationship can do and sleep together. The morning after, Barney realizes that he really cares about Robin and wants to be with her.

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So, they agree to both tell their respective partners about the affair and get together. Barney tells Nora, but Robin doesn’t tell Kevin, and when Barney excitedly waits for Robin to meet him at MacLaren’s, we feel his pain when he sees her come in with Kevin and shake her head at him.

2 When the Mother’s death was foreshadowed

Midway through the final season of How I Met Your Mother, fans started to pick up on the hints that the Mother had been dead the whole time. Her actual death in the series finale didn’t have anywhere near as much impact as this early moment of foreshadowing.

Ted is telling the Mother the story of when it was unclear if Robin’s mom would come to her wedding and she says, “What mother is going to miss her daughter’s wedding?” Seconds later, Ted is holding back tears... and so are we, especially on re-viewings when we know for sure what this was hinting at.

1 When Marshall’s dad died

Of course this one tops the list. On every rewatching, even though they can see the moment coming the second they see the episode-long countdown begin, How I Met Your Mother fans choke up when Lily tells Marshall his dad is dead. Jason Segel’s reaction to the gut-wrenching news has a tragic layer of ingenuity, because he wasn’t told what the twist ending was.

Until they actually shot the scene, he was under the impression that Lily would get out of her cab and tell him she was pregnant. When she tells him his dad has died, his reaction is completely authentic, and they nailed it in one take.

NEXT: How I Met Your Mother: The 5 Best (And 5 Worst) Episodes

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