Cry's video "Hey Kid" made for his niece the day she was born. It starts out adorably awkward as he tries to find what to talk about, and it stays adorable throughout the whole thing.
Nearly any scene with Cry and Clementine in his Let's Play of The Walking Dead.
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...
His playthrough of Fragile Dreams at the end when Seto hears the voices of his companions urging him forward. Especially his affection toward PF when a lot of the fans give her flack.
While playing 'Burial At Sea', he sees the gay NPC couple.
Cry: Awww! I'm glad you two found each other.
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.