- And all of the consequences after, especially in 2.2.
- Bitty is fully convinced that Jack is straight when he realizes he has romantic feelings for him.
- Bitty casually bringing up the fact that the football team locked him in a closet overnight when he was in seventh grade. At the oldest, he would have been thirteen. And he was locked in a closet overnight by a bunch of football players. They locked a gay kid in a closet. No wonder he's so wary of jocks.
- Jack Zimmermann. His past, his present, his issues with his dad, his anxiety disorder, the draft, the pills, and even the above-linked incident, which he blames himself for... basically, literally everything about Jack is upsetting. Readers are praying for the day he just gets the chance to be freed from his worries, realize how much of a gem he is, and how many people love and trust him.
- Notable mention to 1.18. Jack getting chewed out by the media, who put his recent accomplishments aside to talk about how much of a disappointment he was during his addict days. Despite Shitty yelling for someone to "turn that shit off," the damage is done and Jack leaves the room with an utterly heartbreaking look on his face.
- And let's not forget 1.6, aka Jack's backstory, which gives a summarized account of Jack's messed up childhood, in the form of a fairy tale that depicts Jack as a fallen prince trying to reclaim his former glory. The storybook layout of the chapter gives it a childlike sense, which makes watching young Jack go through all that hell a thousand times more painful.
- Remember Kent Parson? Jack's ex-best friend, who was the first pick in the draft when Jack instead went to rehab, and who went on to win a Stanley Cup and Calder Memorial Trophy? Yeah, turns out Jack and Kent were probably in a romantic or sexual relationship (YMMV on whether or not it was abusive), which we find out when Kent reacts to Jack telling him to get out for insulting the Samwell team by deliberately saying things designed to hurt Jack as much as possible.
- Oh, and let's not forget that this results in Jack having a panic attack after Parse finally leaves.
- Samwell makes it into the Frozen Four during Jack and Shitty's last season with the team, but they lose in the finals. Post-game, Bitty notices Jack is missing from the dressing room and finds him crying alone in the loading bay. This is immediately followed by a Heartwarming Moment, when Bitty hugs and cries with him.
- Year 3 keeps implying that Bitty has doubts about his relationship with Jack, and believes that it will come the day when the relationship will end because Jack choose his career over Bitty.
- The entirety of 3.9 is Bitty being insecure and hurt about hiding his relationship with Jack while he has to hear everybody saying how "good friends" they are, how the media badmouths him and how he feels guilty over hiding things from his friends and being unable to get his back.
- Bitty talking about not being out to his parents. Just... ow.
Tearjerker / Check, Please!