How I Met Your Mother/Tear Jerker

• HIMYM is usually one of the happiest shows around... but dammit, it can make you cry like a baby:
  • 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 get's this troper every time.
• 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.
• Near the end of season three there was a subplot that I still haven't forgiven the writers for: Ted decides to "dump" Barney and Neil Patrick Harris decides to break my shriveled black heart for the next three episodes. Finally resolved with a Crowning Moment of Heartwarming, but terrible while it lasts.
• The ending of Benefits. That is all. Damn you NPH!

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?

• • Definitely seconded. Just the look on his face while Robin remains oblivious...
• 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.

• 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 very sudden, 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.
• 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: (finally losing it) Because if you were gonna be some lame suburban dad, why couldn't you have been that for me?!?

• 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.
• 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..."
• 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.
  • "Really glad."
  • Don't forget the eggnog and the 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."
• 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. This Troper is got by the look on his face every single time.
• The scene where James meets Sam for the first time. The look on Sam's face alone does it.
• What, no mention of Stella leaving Ted at the altar in 'Shelter Island'? That was probably one of the most depressing endings in the series.
  • For this troper, it was the ending of the next episode that brought her to tears.

Future!Ted: And that, kids, was the perfect ending to a perfect love story. It just wasn't mine.

• A lot of occasions regarding the Barney/Robin relationship are this. This troper started crying while watching Of Course. Cobie Smulders does a great job playing the role of The Woobie, and seeing the usually held-together Robin cry definitely tugs at the heartstrings.
• To this troper 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.
    • This one was more 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.
• 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 the Tethercat Principle at work, but poor Patrice...