Tear Jerker / Courier's Mind: Rise of New Vegas

• After finding out that Jeannie May the seemingly kindhearted old care taker of the inn is the one responsible for selling Boone's wife and unborn child into slavery, even The Courier is practically at a loss for words.
• Season 9 Episode 7. The Courier knows that Boone was at Bitter Springs and points out that having his wife and child sold into slavery is not related to the massacre. The Courier suggests that the group might be able to return to Cottonwood Cove and check the slave pens for Carla, before noting that Boone never did tell The Courier how he knows Carla's dead. Just look at how the group reacts to what Boone tells them:
  Boone: Fine! How do I know she's dead? Here it is!
  The Courier: And this is the part where I find out what it's like to get shot in the balls!
  Boone: She… I tracked her down. Southeast, near the river. They were selling her. Saw it through my scope, whole place swarming with Legion. Hundreds of them, bidding for things no man has a right to.
  Veronica: Oh God! I'm don't know if I can do this.
  Cass: Think I'm gonna be sick.
  Boone: I just had my rifle. Just me against all of them…
  Veronica: And?
  Boone: … And so I took the shot.
  ED-E: Shocked/Horrified Beeping
  The Courier: Whoa! Wait a minute here.
  Cass: Be really careful what you say here.
  Veronica: What you did was inexcusable!
  (Later in the exchange)
  The Courier: So I'm guessing waiting for the night and then saving her was out of the question, Boone?]]
  Boone: There was never any saving her. They'd have taken her where I couldn't follow. What I did… That was the only rescue.
  Veronica: Uh-uh. I don't think so.
  Arcade: That was his decision to make, not yours.
  Boone: There was no decision. I was meant to pull that trigger. It was a mistake to think I could escape it.
• Simply put, everything about the season 13 finale. After having gone above and beyond to try and prove to House the Brotherhood is an asset, House shoots him down without bothering to address any of his arguments, instead belittling him as 'just a courier', saying he's an employee who needs to do his job. He proceeds to arm up and have ED-E record a message for the rest of the team, getting them away from the Lucky 38. Then, he pulse guns his way through the 38, laying smackdown after smackdown on House, specifically on how he'd have to betray his team, his family, and how House can't comprehend the idea that anyone could be motivated by anything other than money and power. Finally, he confronts House, popping him out of his life support casket to talk to him face to face, brining one final smackdown to House, acknowledging that he sees House as unsuited to rule for the same way he sees himself unsuited, all of which House brushes aside before cursing him out. The Courier then finishes House with a single bullet from Maria. We then see the speech he left for his companions, where he describes his reasoning and why he sees himself as not only unsuited to rule the Mojave, but also to lead them. He states he will leave the Mojave and likely not return for some time, returning to his routes. Then, we see him headed for the North Passage and Zion National Park.
  • The ending scene also implies that without the Courier to keep them together, his companions and followers all go back to the lives they led before he brought them together, which doesn't sound so bad for some like Arcade, Lilly and Rex but Boone, Veronica and Cass are implied to have gone back to the unhappy lives they led beforehand, with Vernoica stuck with a Brotherhood that refuses to listen and Cass seemingly going back to Drowning Her Sorrows at the Mojave Outpost.
• The title sequence of Season 14, set to "It's a Sin" by Eddy Arnold, unique in that the Courier is singing along, specifically the first two lines of the second verse, overall painting a picture of someone who dearly misses his found family but can't go back to them.
  It's a sin to hide behind this heartache. To make believe I've found something new.
  It's a sin to say that I don't miss you. When people know I'm still in love with you.
  • All throughout the season we get brief glimpses of just how much the Courier misses the friends he made in the Mojave when he encounters something that reminds him of them or makes him wish there were there with him and has to take a moment to remind himself that he's likely never going to see them again.
• Season 14, Episode 9. All of which doubles as Nightmare Fuel. The Courier experiences the very definition of a bad trip after drinking a hallucinogen. He ends up losing periods of time, hallucinates dangerous things, has flashbacks to past traumatic events and is ultimately left utterly unhinged and terrified by the end.
  The Courier: (in terrified whispers) "I'm not going back. I'm not going back. I'm not going back".
  • Special mention goes to his hallucination/flashback of the bunker in the divide, especially his reaction to a message graffitied on one of the walls:
  Message: "You can go home Courier."
  The Courier: That's not funny. That's not funny.
  (increasingly panicked)
  Uh, Cloud if you can hear me I need you to pull me out. Please, now!
  • Followed almost immediately afterward by a hallucination of the Divide, it takes him a few seconds to realize where he's supposed to be and when he does.