- Ezmerelda's death in episode 31. A Hunter of Monsters, she was turned into a vampire by Strahd and after his defeat she wanted only to die. Strix gives her a hug and then the exact reason why Ezmerelda has to die is illustrated when she instinctively tries to bite Strix. Despite Diath's advice, Evelyn holds her hand while Paultin beheads her with the Sun Sword.
- The death of Hooty McHootface during childbirth in Episode 36. Strix and Evelyn both break down crying, then the party turns her corpse into jerky.
- The execution, aftermath and subsequent resurrection of the entire Waffle Crew minus Strix in episode 58. Particularly bad since Chris has Holly role-play through some of the 50 years Strix spent alone in Barovia before her friends are brought back, whilst the rest of the crew can only sit and watch.
- Evelyn dies in episode 86, devoured by the Soul Monger but hopefully taking some of it with her in the process by turning into a sun, as well as lifting her friend's Death Curse. Her last action says it all.
- This! So much this. Anna's rendition of "The Parting Glass'' alone will rip your heart out.
- Diath's long overdue Howl of Sorrow at the end of episode 97. Even Chris got misty-eyed.
- Diath again when he described how he first ended up in the Waterdeep dungeons. He had two adventuring partners who he implied he'd also been romantically involved with that betrayed him and left him to be arrested and thrown into the dungeons. It tugged even more at the heart strings when Evelyn asked Diath what happened the first time he'd been in a dungeon, and his immediate response is a quivering, stammered refusal to elaborate.Diath: "I - uh...n-no."
Tear Jerker / Dice, Camera, Action!