After Liz kills herself in The Cat Lady he says that he wanted to be her friend and seems upset over how he couldn't stop it from happening.
In his playthrough of Haunting Ground, Cry takes good care of Fiona's Canine Companion, Hewie. When he's going over the controls for Hewie, he learns that there are a set of commands for discipline. Cry's immediate response?
Cry: Screw that!
Not to mention how horrified and shaken he was when he accidentally kicked Hewie at one point.
Cry: *is hiding Fiona in a corner* I am the worst kind of person...
A small one that requires reading between the lines in his Let's Play of The Wolf Among Us. Back when he played The Walking Dead, he killed Danny St. John with little hesitation, but he then immediately regretted it because Clementine had seen it. In The Wolf Among Us, he got the chance to do the same thing to one of the Tweedles, but chose not to.
Compared to when he first started playing, he really came a long way in his Let's Play of Ōkami, getting invested in the characters and story. In the major Heartwarming/Tearjerker moment of the final boss battle, you can hear him getting choked up in some parts.
Despite the sub-par translation, Cry got really invested in the characters in Forest Of Drizzling Rain, so much so that when he accidentally got the worst ending of the game, he chose to replay it correctly and wound up getting the Golden Ending, which he gleefully described as really touching.
Cry's monologue at the end of his Valiant Hearts playthrough, where he admits he never took history very seriously, brushing it off as unimportant and in the past, never really grasping that they were real events real people had to live through, and that this game powerfully drove home the weight of that reality for him. He didn't expect much from the game, but by the end he loved it.
It is pretty clear from his interactions with young characters like Clementine and Max that he would make a good father.
Cry is featured in Boyinaband's song Spectrum alongside Minx. The song itself is pretty heartwarming on it's own, being a message to all the LGBT+ people who are afraid to speak to their families and friends about their sexuality. But Cry stepping in to add vocals just because it was the right thing to do...Greatest Crowning Moment of Heartwarming of all time.
Him not having Mike shoot Emily in his Until Dawn Let's Play. Especially considering how annoying he found her in the first few videos.
Throughout his playthrough of Undertale he's very audibly charmed by the world and grows attached to all the characters, going for the Pacifist route without even thinking about it.
This bit (especially when you consider he compares Sans to his real-life friend Russ.)
Cry: So hey! Sans is my new friend.
Cry: Never will he not be my friend.
Even though he has expressed annoyance at Alphys in the past, he still likes her.
Alphys: You hate me, don't you?
Cry: Not at all. Not at all, Alphys.
Undertale showed how much of a pacifist Cry really is. Having spared absolutely everyone up until that point, he is at first reluctant to fight Asgore even though the game is actively prompting him to do so, and then...
Cry: How the hell do I do that? I have never even hit anybody in this game.
His reaction to the Pacifist run's credits is absolutely adorable. He giggles and laughs giddily through the entire thing, especially through the Special Thanks section.
Cry's playthrough of Undertale is one gigantic heartwarmer as a whole, with how he gets attached to every single character and the world in the game, culminating to finale when he very audibly gushing about how moving this game is, and it shows with how he narrates Asriel Dreemurr's lines, an audible whisper that sounds like he's in or on the brink of happy tears.
This bit, when fighting Photoshop Flowey.
Flowey: Don't you get it? There's no such thing as happy endings. This is all that's left. Cry: ...I don't believe that.
By the time of the Final Boss of the game, Cry is visibly on the edge of Tears of Joy, especially when he can save the Lost Souls.
Cry donating at least over 4500 dollars during Zeldathon 2015
When Mangaminx's girlfriend proposes to her during a stream with Cry in it, he can be heard softly squealing for a second. When Minx accepts, he is more than obviously very happy.
Cry's LP of Catherine ends with him getting the Lover ending. The end credits are backed by a series of Adorkable snapshots of Katherine and Vincent together with their relationship rejuvenated set to upbeat, triumphant music, and Cry is audibly endeared and amused throughout.
Cry's stream of Transistor has a few heartwarming moments as he gets more and more attached to Red through her humming/singing and the Man in the Transistor, as Cry starts calling him "Buddy" especially when he starts going a little loopy as Cry seems genuinely concerned about his mental health.
Cry: (As The Spine flies by Bracket Tower) Whoa..
Transistor: What...was that?
Cry: Its the thing that made you loopy.
He is also somewhat amused at the Transistors "drunkenness"
Transistor: That's my star. Could always handle yourself. Just fine.
Transistor: I love you so much Red you know that right? Its true. Its true. Its true...
Red:(typing at a Terminal) I'm going to find the thing that's doing this and I'm going to break its heart
Transistor: Go get'em....
Transistor: I believe you...
Cry: Dude. Dude, that was an amazing use of the mechanics here.
Cry: Fuck you, that was touching as shit.
While playing through the opening stage of Shantae: Half-Genie Hero, Cry is very quiet while the game's Theme Song, "Dance Through the Danger," is playing. When he reaches the end of the stage where the music stops, he immediately starts gushing about the soundtrack.
Cry: I know I'm supposed to, like, say words in these kinds of videos? But that was so fucking good! I would've been butchering shit if I was saying anything. God fuckin' damn, dawg. I gotta... I gotta listen to this game's OST.