* In the episode "Chuck Versus the Alma Mater", after Chuck finds out that [[spoiler: Bryce Larkin was protecting Chuck all along and that he never actually betrayed him]], we get a flashback at the end, which shows Chuck and Bryce meeting for the first time, this was pretty heartbreaking, [[spoiler: considering that Chuck thought Bryce was dead at that point.]]
* The episode "Chuck Versus the Marlin". Because of those damn FULCRUM agents, the government decides that Chuck will be taken from his job, family, and friends, and basically stuck in a basement for the foreseeable future. The episode itself is heartbreaking from the get-go, but it hits you square in the gut when Chuck is waiting to be taken away and tries his best to face his fate and is clearly failing. One particularly touching moment was when Chuck said the upside to having his life taken from him, was that maybe perhaps Sarah could visit him in his cell, and maybe see how they really felt about each other.
** Chuck asking Sarah to tell everybody ''something'' to explain why he's gone, instead of just disappearing into thin air.
--> '''Chuck:''' Tell them....I don't know, I....Look, if I'm supposed to be dead just say something that will make it okay, that will make them feel alright. Just make sure they know how much I love them.
* The fountain conversation in "Chuck Versus the Breakup".
* "Chuck Versus the Pink Slip":
--->[[spoiler:'''Sarah:''' It's not that simple. You don't know who you're working for. It's complicated. Nothing is real. This... (''clasps Chuck's hand'') this is simple. This is a real life. We have to go, Chuck. This is it. Are you coming?\\
'''Chuck:''' (''hands Sarah back the train ticket'') I can't. I'm sorry.]]
* ...which makes Chuck's speech in "Chuck Versus the Three Words" all the more poignant:
--->[[spoiler:"Look, Sarah, I know... I know that you're probably very hurt... you're probably hurt that I didn't run away with you in Prague. I did that... I'm sorry. You have to know that you were everything that I ever wanted. But how could do that... how could I run away with you... how could I be with you knowing what I'd turn my back on... you know, knowing what I had in my head could help a lot of people? And you're the one that taught me that being a spy is about choosing something bigger... it's about putting aside your own personal feelings for the greater good, and that's what I chose. I chose to be a spy for my friends and my family and you. I chose to be a spy because... Sarah, I love you."]]
* In "Chuck Versus the Beard", Morgan gets fed up with Chuck being so secretive that he de-friends Chuck. The fact that at this time Chuck was so weighed down by how lonely and conflicted he was that he couldn't even flash properly made an already upsetting moment so much worse.
* "Chuck Versus the Tic Tac" is just one punch in the gut after another, all of them involving Casey and all of them hurting about as much as an actual punch in the gut from Casey would. Not enough to find out that [[spoiler: "John Casey" is really "Alexander Coburn," a soldier who faked his death and took on a new identity in order to serve his country]]? Try seeing [[spoiler: ''yet another'' of his mentors going rogue and forcing him into committing treason to save the life of his former fiancée, who still thinks he's dead]]. And then meeting [[spoiler: the daughter he didn't know he had]]. And just because this episode hasn't been cruel enough to Casey ''already'', it ends with him [[spoiler: being dismissed from service]]. If you never thought Creator/AdamBaldwin could break your heart, think again.
* The little moment at the end of "Chuck Versus the Tooth" just after Chuck's been told by a CIA doctor that the Intersect is [[spoiler: damaging his brain, so that unless a solution is found it will eventually drive him insane and/or kill him]]. He comes home and is steeling himself to tell Sarah, just as she, looking blissfully happy, finally tells him flat-out that she loves him, which he's been wanting her to do all episode. He has the most heartbreaking look on his face for a split-second before going into StepfordSmiler mode and saying he's been given a clean bill of health.
* "Chuck Versus the Subway": [[spoiler: Shaw murders Chuck's father right in front of him, with Ellie watching the whole thing from her hiding place. Just so that Chuck wouldn't be able to use his Intersect-given fighting skills.]]
* "Chuck Versus Phase Three" had [[spoiler: Sarah, after tearing apart much of the jungles of Thailand, finding Chuck nearly lobotomized. In tears, she finally tells Chuck what she needed to tell him:]]
--->[[spoiler:"Chuck, I want to spend the rest of my life with you. I don't care if you have the Intersect or not. Without you, I'm nobody. I'm nothing but a spy. Come back to me, Chuck. I want to marry you."]]
* The beginning of "Chuck Versus the Cliffhanger" when [[spoiler:Sarah is rushed to hospital after being poisoned by Vivian]]:
-->[[spoiler:'''Sarah:''' ''(delirious)'' Chuck?]]
-->[[spoiler:'''Chuck:''' Hey. Hey, baby, hey, I'm right here.]]
-->[[spoiler:'''Sarah:''' You look worried.]]
-->[[spoiler:'''Chuck:''' No, you know, just... it's just wedding stuff.]]
-->[[spoiler:'''Sarah:''' [[BorrowedCatchPhrase Don't freak out.]] We're ready for it. ''(Her eyes close)'']]
-->[[spoiler:'''Chuck:''' Sarah... Baby, I'm going to fix this. We're going to get married and be together. Forever. I love you.]]
* The last several minutes to "Chuck Versus The Bullet Train" were absolutely gutwrenching.
** To elaborate [[spoiler: Sarah, who was suffering the effects of the Intersect (namely agonizing headaches and memory defects), goes after {{Big Bad}} Quinn who's being pursued by Chuck and Casey. She confronts him in the back car of the train only to be tranquilized by Quinn. Chuck watches helplessly as Quinn separates the car from the train, taking off with his wife, [[YankTheDogsChain just as they were about to quit the spy business and start a life together]].]]
*** It goes FromBadToWorse. [[spoiler: Sarah is taken to a warehouse where Quinn completely wipes away her mind, making her forget everything, including Chuck. Keep in mind, that it's as terrible as it sounds, with Sarah suffering physical and mental torture as this is happening. Sadly, Chuck and Casey track her to the warehouse, but arrive too late.]]
**** [[KickTheDog And the icing on the cake.]][[spoiler: Quinn plans on using the new, {{Mind Rape}}d Sarah to kill Chuck.]]
* Think that's bad? The succeeding episode, "Chuck Versus Sarah" (and no, it's not a [[ExactlyWhatItSaysOnTheTin metaphorical title]], so...) is far worse, especially the last half of the episode. To put it simply, if you think Zachary Levi couldn't make you weep buckets? Think again.
** To further elaborate, [[spoiler: The last half has Chuck taking Evil!Sarah to their dream house, and desperately trying to restore her memories, as he tearfully tells Sarah about the great times they've had together over the past five years.]]