The ending of "Come On". Seeing Ted arriving home so happy only to find Marshall sitting on their building's doorsteps, in the rain, holding Lily's engagement ring.
Lily telling Ted she's having doubts about marrying Marshall and telling him why she wants to go to San Francisco in "Milk". Aly's acting in that scene is perfectly heartbreaking.
The ending of "The Limo." Ted gets his kiss from Robin, but it doesn't exactly feel like the happy and victorious moment we were rooting for.
The last scene of "Slutty Pumpkin," while sweet, is also quite sad as it shows how much Ted wants to find a special someone, and how much Robin wants to want to find a special someone. The song playing in the background involves the lyrics: "I wanna know what's like on the inside," playing overtop Marshall and Lily, which sums up the situation quite well.
Ted and Robin's break-up at the end of season two is gut-wrenching since it comes about because they love and care for each other too much. It wasn't a petty fight, misunderstanding or a conflict of feelings that split them up, but just the realization that they had been ignoring those signs they had "an expiration date." The first thing they did when they made the decision was hold each other and tear-up.
Robin: "You stole a french horn for me..." Ted: "I would have stolen a whole orchestra."
Ted decides to "dump" Barney and Neil Patrick Harris portrays Barney as absolutely devastated over losing his best friend. Finally resolved with a Crowning Moment of Heartwarming, but terrible while it lasts.
Everyone reacting to the news that Ted was in a car accident at the beginning of "Miracles".
In "Do I Know You?", Barney is trying to make Robin see him as a more thoughtful, boyfriendable kind of guy. They have a dinner and Robin expresses her enjoyment of the evening before excusing herself to the loo just as Barney is about to tell her he likes her. Robin returns...with the waitress, wingmanning for Barney as thanks for his listening and being such a good dinner guest.
Stella leaving Ted at the altar in "Shelter Island". One of the most depressing endings in the series.
Future!Ted: And that, kids, was the perfect ending to a perfect love story. It just wasn't mine.
Barney singing "Cat's in the Cradle" at the end of Not A Father's Day is mostly Played for Laughs, but it gets a lot sadder when you really think about what that song is about. Especially after you watch season six.
The ending of "Benefits". Just the look on Barney's face while Robin remains oblivious to his love confession.
Robin: He can't separate the physical from the emotional. He's all like...
Barney: I love you.
Robin: (misunderstands him and thinks he's talking about Ted) ... exactly! He's not like you, you know?
Ted and Lily's extremely tense screaming match in "The Front Porch" after Ted realizes that Lily broke him and Robin up. Even though everything's forgiven in the end, it was like watching your parents fighting and threatening divorce.
Ted's speech to Stella in As Fast As She Can, about how he wants what Stella and Tony and Lily and Marshall have, but is tired of looking and waiting.
Ted: Okay, I'm gonna say something out loud that I've been doing a pretty good job of not saying out loud lately... what you and Tony have... what I thought for a second that you and I had... what I know that Marshall and Lily have... I want that! I do. I keep waiting for it to happen and waiting for it to happen, and... I guess I'm just, uh... I'm tired of waiting. And that's all I'm willing to say on that subject.
Stella: (...) I know that you're tired of waiting and... you may have to wait a little while more, but... she's on her way, Ted! And she's getting here as fast as she can.
Ted: (smiling softly) Goodbye, Stella.
Stella: (near whisper) Goodbye, Ted.
Robin's emotional breakdown after Don leaves her to take a job in Chicago (and, to add salt to the wound, it's the same job she turned down because she wanted to remain with Don), and her begging Ted to let her be his roommate again.
Even before that, the montage in "Of Course" revealing just how hurt Robin is that Barney is rubbing his "conquests" right in her face (and Ted and Marshall joining in) so soon after their breakup. And right when it looks like she might be moving on, Barney and Ted inadvertently make it worse with the Superdate thing, something Barney never did for Robin. No wonder the guys felt as guilty as they did!
The scene where James meets Sam for the first time. The look on Sam's face alone does it.
The ending of "Bad News" where Marshall learns that his dad had a fatal heart attack. The look on Lilly's face alone was enough to make you cry. Then you notice that Marshell is trying to be strong and failing.
Marshall: (breaking down in Lily's arms) I'm not ready for this.
Jason Segel and Alyson Hannigan both REALLY sold this scene. It's verysudden, and it hits hard.
Segel's performance in particular is amazing, as in rehearsals Lily told him that she was pregnant. The producers prepped Hannigan immediately before the scene, and kept Segel in the dark. His reaction was entirely unscripted.
Marshall's breakdown outside of his father's funeral in "Last Words." Brings out all the emotions that run through a person in that circumstance.
At the end of 'Change of Heart', when Lily has finally convinced that Barney has actual feelings for Nora, he shows up where she is having brunch with her parents, and the scene goes on to show him going inside, apologizing for telling her he wasn't interested, and being introduced to her parents. Alas, it's just an imagination spot, and the look on his face when it pans back to him standing out there and giving up is just heartcrushing. To top it off, just after he walks away, Nora looks up and has missed him, also with a look as if she wished he were in there.
Barney's emotional meltdown at the basketball hoop in the end of 'Legendaddy'. To elaborate, he has very recently had his father (who abandoned him when he was six) come back into his life and try to reconnect with him. Barney was hoping his father, Jerry, would be a hard-partying roadie who wasn't capable of being a father, since this would justify him abandoning Barney. However, Jerry has turned out to be a loving dad with two children, including a boy named 'Jerome Junior'. Barney can't handle this, and it culminates into him trying to yank JJ's basketball hoop off the garage so he could have at least some souvenir of a childhood he never got to have. Particularly heartbreaking is this exchange:
Barney: You're lame, okay? You're just some lame suburban dad.
Jerry: Why does that make you so mad?!
Barney: Because if you were gonna be some lame suburban dad, why couldn't you have been that for me?!?
Seconded. NPH's delivery of that line will break you.
In "The Exploding Meatball Sub", when Lily is about to head off to Spain because supporting Marshall through his oblivious insistence on quitting his job and taking up ridiculous projects while volunteering for the NRDC is driving her crazy. Ted is rightly appalled, furious, and clearly terrified (for although he doesn't mention it, the memory of Lily breaking for San Fransisco is clearly in the forefront of both his and the audience's minds), until in the middle of Lily's rant, she breaks down into tears and confesses that she's afraid that Marshall doesn't want to have a baby with her anymore. Ted's demeanor immediately dissolves into tenderness with a soft "Oh Lil..."
Barney confessing to his father how unsure he is of improving his bachelor lifestyle and admitting he is too far gone and broken.
Turns to a heartwarming moment, when his father quickly turns around and reminds him that it is possible to become happy in life just by meeting the right women.
Marshall's conversation with his late father about being unable to see his future and his revelation that his father was fallible but still an inspirtation in "Desperation Day"
The season seven opener as Robin tells Barney what to tell Nora... and she's really saying it to him and he's completely oblivious. Then he thanks her for getting him a second chance with Nora and walks away.
At the end of 'Tick, Tick, Tick...'
Future Ted:...for Barney, the second that would never end was this one..."
After realizing that Robin has chosen Kevin the look on Barney's face is absolutely heartbreaking. Then the icing on the cake? Watching him clean up the bedroom he had decorated with rose petals and candles.
In 'Symphony of Illumination' Robin is narrating the episode to her and Barney's future kids. Until she finds out she can't ever have children. "So I can't have kids. Big deal. This way, there's no one to hold me back in life. No one to keep me from traveling where I wanna travel, no one getting in the way of my career. If you wanna know the truth of it, I'm glad you guys aren't real." And the kids fade away.
Plus Robin's Thousand-Yard Stare when it cuts to her sitting alone on the park bench, with said eggnog in said snowstorm.
And Robin dissolving into tears in Ted's arms after he tells her that he'll never stop trying to cheer her up even if she can't tell him what's wrong, and clinging to him wordlessly while Future!Ted somberly reveals that "Your Aunt Robin never became a pole vaulter."
There are two particularly gut wrenching moments in the episode "No Pressure''.
The scene where Barney tells Ted that after Robin had broken his heart and chosen Kevin over him, he no longer has feelings for her.
Later on, the scene where Robin tells Ted that she will never love him as anything more than a friend. It was bittersweet, as Ted hadn't exactly been pining for Robin: he had been wondering whether or not they should get back together, and despite the finality being painful, he was relieved that he could move on. However, that doesn't make the scene where he's standing on the roof staring depressedly out into the city as Robin moved out of the apartment any less saddening — after all, he doesn't know the mother is out there.
The way she tears up a little and is choking out her "no" indicates that Robin knows it's not the answer Ted is hoping for.
The music, the paradoxically triumphant and heartbreaking Shake It Out by Florence and the Machine sums up the whole situation nicely. And heartbreakingly.
Super minor, but Patrice in "Karma"... sitting there, excitedly waiting for Robin to come, only Robin A: hates her and B: isn't coming anyway. It's pretty much Offscreen Inertia at work, but poor Patrice...
Barney's "Robin-box" and her reaction when she finds it.
In "Nannies", all episode long, Lily and Marshall search high and low for the perfect nanny to babysit their kid, Marvin. Lily's father wants to volunteer but Lily is reluctant because of all the years her dad has neglected her. When Marshall and Lily think that Marvin has gone missing, they find out that her father had Marvin all along and took really good care of the child. Mr. Aldrin then explains that while Lily's mom was off working, he was the stay-home dad and that her grandparents only came to visit, instead of her grandparents taking care of her as Lily saw it. It is then revealed that Mr. Aldrin had managed to save a photo album from a fire that burned down their house which is told earlier in the episode. The photo album then reveals all the times Mr. Aldrin shared with newborn Lily, capping it off with Lily's first day of preschool. Mr. Aldrin then apologizes to his daughter for all his neglectfulness and promises to be around for Marvin, if Lily is fine with it. Lily then decides to make her father the new nanny and a slideshow is shown of the moments Lily, Marshall, their son Marvin, and Mr. Aldrin shared, the slideshow ending on a picture of Marvin's first day of preschool.
You have to feel sorry for Ted after Jeanette completely destroys his apartment, complete with him solemnly saying he's finally ready to settle down.
The Reveal for "The Time Travelers." The whole episode was an Imagine Spot for Ted. While all of his friends are moving forward in their lives, Ted is sitting in Mclarens, probably never this alone in his life. Becomes a heartwarming moment when he discusses what he would do if he had traveled back in time to that night: Meet The Mother weeks before they actually do and tell her that he wishes that they could spend the time before they meet together so he wouldn't be alone.
"Hi. I’m Ted Mosby. And exactly 45 days from now, you and I are gonna meet, and we’re gonna get married, and… We’re gonna have two kids. And we’re gonna love them and each other so much… All that is 45 days away. But I’m here now, I guess, because… I want those extra 45 days with you. I want each one of them. And look, if I can’t have them, I’ll take the 45 seconds before your boyfriend shows up and punches me in the face, because… I love you. I’m always gonna love you. Till the end of my days… and beyond. You’ll see."
Since "The Time Travelers", Ted has experienced a bad Despair Event Horizon that slowly occurred and basically hit rock bottom in "Something New". Ted's willing to move to Chicago after the wedding just to stay away from Robin, someone who he loves dearly, because she's married and seeing her just reminds himself that he is unable to find the one for him. It makes you feel for him so damned much. Luckily though, the Mother finally shows up on her way to the wedding. He also seems to feel guilty over his feelings for Robin, since he knows she's marring one of his best friends, heck maybe he wanted to move to Chicago because he didn't want to get in the way of Barney/Robin.
Ted: That's just a really sucky way to feel about your best friend's fiancée.
A fair amount of HIMYM fans seem to dislike Ted, feeling he's boring and/or unsympathetic, but the last few seasons have to have done a decent job of making him more sympathetic. Beginning with his relationship with Zoey ending really badly and his admission to Robin early in Season 7 that he'd been feeling a bit jaded about finding someone, the Slutty Pumpkin and Victoria also returned only for both relationships to fizzle and leave Ted feeling disillusioned. That was followed by Robin admitting that she didn't love him romantically and then getting engaged to Barney, the fling with Jeannette which was a huge, self-destructive disaster and the guilt over lingering feelings for one of his best friend's fiancee. Seeing as how it's at the point where Ted is ready to just quietly leave New York and all his friends behind as he feel there's nothing left for him and he doesn't want to get in the way of Barney and Robin, it wouldn't have been a surprise if Future!Ted's narration had admitted to his kids that at that moment, he'd pretty much given up all hope of ever meeting their mother, having hit rock bottom. Fortunately, we know that the story has a happy ending, but Ted's had to go through some really dark times to be in the right spot and the right person to meet The Mother.
Ted getting "one last life lecture" from Lily before he leaves for Chicago. (Though, of course, we all know he won't reallyleave New York, and, as Lily puts it, he's dreaming if he thinks this is the last one)
Lily: You wrote all of these things to say goodbye to, but so many of them are good things. Why not just say goodbye to the bad things? Say goodbye to all the times you felt lost, to all the times it was a "no" instead of a "yes," to all the scrapes and bruises, to all the heartache. Say goodbye to everything your really want to do for the last time, but don't go have one last Scotch with Barney, have the first Scotch toasting Barney's new life, because that's a good thing and the good things will always be here waiting for you.
The look of quiet despair on Ted's face as Barney finishes his story of how the Mother (whom Ted still hasn't met yet) inspired Barney to win over Robin with everything he's got because that night was also the same night Ted had his last Hope Spot that he could win over Robin.
Ted and Barney's fight about Chicago is just so utterly painful for both of them. Barney initially thinks Ted not telling him was because he didn't care, and we all know he has huge abandonment issues as it is. But Ted does care, he just doesn't want to take away from the happiness of his two best friends getting married, even though though he's leaving becausethey're getting married. True, Ted does steal the Glen Mc Kenna to make up for it and Barney does accept his decision, but even then they still have to say goodbye to each other. The "I'm going to miss you" and the hug really did it.