Top 10 Saddest How I Met Your Mother Moments
#10: Tracy Talks to Max “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.
#9: Lily Leaves Marshall “Come On”
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“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.
#8: Lily’s Confession “Band or DJ?”
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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.
#7: Barney’s Longest Second “Tick Tick Tick”
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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.
#6: Marvin Sr.’s Funeral Voicemail “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.
#5: Barney Stealing the Basketball Net “Legendaddy”
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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. #4: 45 Days “The Time Travelers”
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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.
#3: Tracy’s Death “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.
#2: Robin Can’t Have Children “Symphony of Illumination”
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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.
#1: Marshall’s Dad’s Death “Bad News”
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… 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.
