- Louis's cat dying. Anyone who has or had a cat will understand why he looks like his world has crashed.
- Donna getting fired. The look on her face is just heartbreaking. Even though we know she'll end up coming back one way or another, it's still heartbreaking.
- Mike's grandma dying. His face when Rachel tells him is just devastating. Doubly so because he was finally making enough money to be able to properly take care of her and had just bought her an apartment when Rachel comes to see him.
- In Season 3, when Louis tries to befriend Mike, after Harvey had been an unforgiving jerk to him since the season 2 finale, with Harvey's blessing. By the episode's end, Harvey forgives Mike and Mike goes back to Harvey at the first opportunity... after he just told Louis he would join him. You can just see Louis's heart breaking as he walks up holding a cake, which he ends up throwing away. It had "Welcome to Team Litt" written on it. Sniffle.
- Louis... just Louis in the scene in episode 4x04 where he tells Harvey that Mike getting Forstman to fund his plan because of something that Louis told him, when he went to stick it to him. The conversation is heartbreaking and Louis is nearly in tears:
Harvey: Goddamn it, Louis. I don't wanna keep being mad at you, but you keep doing the same shit.Louis: But you see, this wasn't me being duped.Harvey: No. It was you letting your emotions lead you into doing something stupid Again. You just had to stick it in his face. You know what? I'm done.Louis: (visibly holding back tears) It's not fair, you know. I'm emotional. You're cold. You're loved. And I'm hated.
- Season 4 does another to Louis. To be the hero, he had to break the law. The law comes biting back and the only way to save himself would be to frame Harvey. While Louis can be slimy, he's not that slimy yet of course going to prison for a fairly significant felony and destroying his life is obviously not the most thrilling option either.
- The flashback to young Michael coming down the stairs to find his grandma waiting to break the news of his parents dying in a car crash.
- The entire episode of Faith, culminating in this conversation:
Mike: Harvey, you didn't just give me my dream. You gave me a family. But I'm gonna have a family of my own someday, and I can't have all of this hanging over their heads.Harvey: You're resigning.Mike: I am.Harvey: You know, you once asked me why I hired you, and I told you it was because life is like this and I like this.Mike: Harvey, please, you can't convince me—Harvey: Let me finish. It was like this not because of the risk we're taking. It's because of who you are.Mike: So you're not disappointed?Harvey: Are you kidding me? After that speech, if you hadn't done this, I'd be kicking you out. And for the record, you're not the only one who got more family out of this deal.
- The season 5 episode 25th Hour is full of these, but a special mention has to go out to the revelation that the verdict about Mike would have been not guilty.
- In "Character and Fitness" when Tara breaks up with Louis over voicemail. Louis is devastated and breaks down. Doubles as a moment of heartwarming as Rachael puts her arms around Louis and comforts him.