Top 20 Saddest How I Met Your Mother Moments

“Last Forever: Part 1”

Much of the last season of “How I Met Your Mother” – and indeed, the last few seasons of the show – are geared towards Robin and Barney, specifically their wedding. That’s why this moment is such a gut punch! When the gang gets together to talk about how things are going, Barney and Robin reveal they’ve been having problems. After a flashback demonstrates that their way of dealing with them isn’t exactly healthy, the two explain that they’ve divorced. While many marriages don’t work out, we still hoped that Barney and Robin would be able to make theirs work, particularly after all that build-up.

“A Change of Heart”

Barney doesn’t seem like the type to settle down. That’s why, when he tells his girlfriend Nora that he does, we believe him when he later confesses otherwise. When it turns out to have actually been the truth, however, Barney sets intentions to make amends with Nora and tell her that he does want to settle down. He finds her at a cafe, apologizes, and they reconcile. Except…the camera pans over and reveals that the whole scene was in Barney’s imagination. In reality, he walks away. It’s a sad scene because it’s so relatable. How many of us have imagined happiness for ourselves, but not pursued it or self-sabotaged for one reason or another?

“Last Forever: Part 1” & “Last Forever: Part 2”

Following Robin and Barney’s divorce, the group worries that they’ll drift apart as friends often have to choose sides when couples break up. Lily makes sure to secure promises that they’ll be together for the big moments. However, despite this promise, Robin ends up estranged from the group throughout the years afterward since her job leads her to travel the world, while the rest of the group stays closer together. It’s a sad reality that people who were once close friends often grow apart from each other, but it still hurts to see it happen to Robin and the group.

“The Goat”

Barney and Robin sleeping together complicates things for both of them, and not just because they’re friends. At this point, Robin and Ted had already dated, and dating the ex of a bro goes against Barney’s much-vaunted Bro Code. It also doesn’t help that this whole thing takes place shortly before Ted’s birthday. While Barney looks for a loophole in his dubious legal document, he ultimately decides to own up. Except, Ted already knows. Ted’s extended rant on the subject does have its funny moments, but eventually he posits that, much like a box of things he’s getting rid of, he’s considering Barney’s worth to him too. Barney and Ted do reconcile eventually, but it’s still sad to see Ted sever their friendship temporarily.

“The Autumn of Break-Ups”

Among Ted’s many relationships throughout the show, arguably the third most important, after Robin and the Mother, is Victoria. After a long period apart, the two of them get back together, and Ted even proposes. However, Victoria is insistent that Ted break off his friendship with Robin, since she’s the reason they broke up the first time. Ted reluctantly agrees, but when the time comes for him to tell Robin, he can’t do it. Instead, he tells Victoria that Robin is like family to him and asks if she can handle that. She can’t, and she breaks up with him for good. Ted’s lingering attachment to Robin causes him a lot of heartbreak during the show and our hearts break along with him here.

“Shelter Island”

Ted doesn’t have the best luck with weddings. Still, he doesn’t help his track record when he invites not only his own ex, Robin, to his wedding with Stella, but also Stella’s ex, Tony. Stella is upset, telling Ted she’s worried about his lingering feelings for Robin. However, ultimately, when Ted finds a note from Stella, it turns out she was merely projecting her own worries about her ex. Stella leaves Ted at the altar to go off with Tony. While it’s easy to say that we want the person we love to be happy, it still cuts like a knife when their happiness means not being with you.

“Unpause”

Marshall and Lily have a fantastic relationship – for the most part. One of their biggest and only fights occurs in the final season, when Marshall applies for a judgeship without consulting Lily. Despite their attempts to put the fight on pause, they can’t delay it forever and they eventually explode. Lily is understandably furious that Marshall didn’t tell her, particularly with their trip to Italy planned. Meanwhile, Marshall reiterates that the opportunity was time sensitive, and his dream. Lily insists that she has never been so selfish, but Marshall brings up a good point - she has. Both of them are in the right and in the wrong at the same time, so it tears us apart watching them fight.

“Last Forever: Part 1”

Ted has a hard time handling Barney and Robin’s wedding, so he decides to move to Chicago. To that end, he leaves the reception early. On the patio outside, he and his friends say what they believe will be their last goodbyes for a while. Each goodbye is emotional in itself, with callbacks to many episodes throughout the show. But they all happen one after the other! While this isn’t the end of the show, or their friendships, it still makes us teary-eyed to look back on everything they’ve been through. Not to mention, Lily crying makes us cry! At least Ted and Barney get in an epic high-five.

“No Pressure”

Ted’s love for Robin is persistent, as we’ve mentioned (and will continue to mention). After laying it all on the line with her, Ted is despondent, even if he refuses to acknowledge it himself. Despite Marshall believing that the two will end up together (if only for the purposes of a bet with Lily), he can still see that Ted is hurting. Marshall tells Robin what Ted is unable to – she needs to move out of their apartment. It’s the end of an era for the two of them but at least it opens up some new possibilities for Ted – and it’s a great musical moment for the show, too! Even so, this gesture isn’t enough for Ted, something his move to Chicago proves in the end.

“No Pressure”

This one comes right off the tail of the last entry, but we thought it deserved its own mention. After some confusing feelings and a kiss, Ted’s feelings for Robin are rekindled. He declares several times to Robin that he loves her. While she waffles, Ted insists on a definitive answer. And she gives him one, just not the one he’s hoping for. Even if you’re not a fan of their relationship, seeing Ted get shot down after being so vulnerable is still tough to watch. It hits even harder when we see it again in Ted’s montage of all the worst times he’s been hurt in his life, considering it ranks right at the top.

“Come On”

“Marshmallow and Lilypad” are the kind of couple that we all aspire to. Their communication, support, and general adorability are all fantastic to watch. So when Lily accepts a fellowship across the country without telling Marshall in the season one finale, their ensuing fight is rather unexpected. Although the two try to delay having to deal with the issue by pausing their argument, eventually they break up; leaving Marshall crying in the rain. Even this early on in the series, these two seemed like they would be together forever, so their seemingly permanent break-up hits home.

“How Your Mother Met Me”

The titular mother, Tracy, has her own journey towards Ted Mosby, and it’s a tragic one. In her early 20s, Tracy’s first love, Max, dies abruptly. She takes many years to get over the loss, though she eventually does start dating again, even if her boyfriend Louis isn’t exactly perfect for her. When Louis proposes, Tracy takes a moment in private to speak to Max, asking permission to move on. While she rejects Louis, she plays a rendition of “La Vie en Rose” on the ukulele in a bittersweet and beautiful moment that Ted bears witness to. Also, Tracy’s lost love is foreshadowing for a later entry on our list.

“Band or DJ?”

Barney and Robin’s wedding, particularly its planning stages, proves to be a stressful time – and not just for them! Ted especially becomes stressed as he tries to reconcile his feelings for Robin with his attempts to be a good friend. Ultimately, Lily sits him down on the roof to get him to admit to this and in doing so, she admits something even worse – sometimes, she wishes she wasn’t a mother. She admits that working with children and being a mother makes it all feel like work and that she sometimes fantasizes about leaving her life behind. Feeling trapped by what you love is sadly a very relatable experience.

“Tick Tick Tick”

Barney and Robin had a long and difficult path to get to the altar. Following their first attempt at a relationship, they each cheat on their partners to sleep with each other. Although both feel guilty, and attempt to confess their indiscretion, Barney believes that he and Robin can still get together once they have ended their current relationships. However, although Barney breaks up with Nora, Robin does not tell Kevin; and Barney’s realization that she doesn’t feel the same about him leaves him feeling like time has stopped. While time is frozen, we’re right there with him. And him cleaning up the rose petals right afterward only adds insult to injury!

“Last Words”

Marshall’s father, Marvin, tragically passes away midway through the series, naturally leaving Marshall devastated. During his funeral, Marshall discovers he has one final voicemail from his father and while he puts off listening to it, he eventually can’t take it anymore…only to be disappointed that it’s a pocket dial. He goes on to express what his father meant to him and how he feels robbed of a chance to hear his final words…only for his father to realize that his phone was on, and tell his son he loves him one final time. This moment is a tearjerker, but they’re both sad and happy tears.

“Legendaddy”

After years spent in ignorance, Barney finally meets his father. While in typical Barney fashion, he first tries to play up his father’s accomplishments, turns out he’s actually just a typical suburban dad. During a dinner with Jerry and his family, Barney mocks his half-brother and storms out; ineffectually trying to steal the basketball hoop and backboard above Jerry’s garage. When Jerry tries to find out why Barney is disappointed in Jerry’s suburban lifestyle, Barney tells him that he wants to know why Jerry couldn’t have been a dad to him growing up; he only wants the net as consolation. Neil Patrick Harris’ acting is excellent and we really feel for Barney here.

“Symphony of Illumination”

At first upset at the prospect of having kids, Robin is relieved when she’s told she won’t be having a child. But Robin is still surprisingly affected when the doctor later tells her that she can’t have children...at all. She tries brushing it off, but she becomes more upset as the episode goes on, and the feels are further piled on when it’s revealed that the children she’s been narrating to aren’t real. This culminates in her breaking down into tears at Ted’s attempt to cheer her up.

“The Time Travelers”

After a night spent in the bar with hypothetical future versions of himself and Barney, Ted realizes that he’s actually been there alone, lost in reminiscences. Future Ted tells his kids if he really could change the past, he would do many things, but the first thing he’d do would be to visit their future mother. He then imagines himself rushing to meet Tracy, giving her an emotional speech, telling her how much he’s going to love her when they meet in 45 days, and saying that he wishes he could have that extra time with her. The moment is performed brilliantly and is made all the more heartbreaking given our next entry.

“Last Forever - Part Two”

Although the death of Tracy is foreshadowed several times during the series, including the previous entry, as well as in that scene at the restaurant, Tracy’s death still packs an emotional punch. During the finale, just prior to finally telling his kids how he met her, Ted reveals to the audience through a montage that Tracy got sick through an unspecified illness and passed away 6 years before he started telling his kids the story. While we may have only spent a season getting to know her, Tracy was a great character and a pivotal part of the show, and losing her really hurt.

“Bad News”

We’ve already seen what the aftermath of Marshall’s dad’s death does to him, but the moment he finds out is easily the saddest part of the entire show. Marshall and his dad are incredibly close, despite living so far apart, so Marshall struggles with whether to tell him about the fertility issues he and Lily are having. After learning he and Lily can have kids, Marshall attempts to call his dad to no avail, and when he meets up with Lily, she tells him his father had a heart attack and died. Marshall’s devastation is incredibly authentic, and we’re all the sadder because of it.