It's downright morbid. I always compared it to uncle Rico from Napoleon Dynamite, a 40+ year old man obsessed with his high school football career enough too seriously ask his nerdy nephews if time travel could help him go back. (I do believe Chris has mused on time travel once or twice himself.)
I don't know. Chris does go over the top, but being nostalgic for good times in the past is pretty common. And you have to allow for the fact that Chris' life hasn't gone very well since, and when the present sucks, you dwell in the past.
Chris does over glorify his high school days and wish he could go back and change/relive them. Which is kind of silly, but is also pretty common. His high school nostalgia always struck me as a fairly normal sentiment filtered through a weak and inarticulate mind.
It just goes to show that befriending Chris is something of a lost cause. Girls who try are immediately targeted as the next Sweetheart and no amount to telling him to quit it seems to at all do the trick. Part of this may be his autism kicking in since he cannot take social cues but when he is told time and time again that his advances are not welcome and he still ignores it, it becomes nothing short of either stupidity or deperation. Perhaps a mixture of both? Or is he so deluded he thinks no girl can ever hang out with him without eventually falling in love with him (despite that never having happened)?
As for guys who try, they tend to be ignored and only tolerated if they are friends with a Sweetheart-to-be.
He views getting a sweetheart/sex partner as his number 1 priority, so other types of relationships are frustrating to him. He struggles socially, so he doesn't have good relationships with a lot of women. When he gets along with one of them, but she doesn't want to be his sweetheart, he feels like it is a waste of an opportunity.
A lot of the time his thinking seems to be "we are supposed to be friends, and you have the ability to make me much happier by being by sweetheart, but you won't do it. That's bulllshit."
He's got live employees telling him that it's stealing, but he makes up some nonsense about a sign being needed. I remember he got mad when we suggested that anyone could walk into his house and take his toys because he didn't have a sign prohibiting it. He loves to be a childish rules lawyer when he thinks it'll excuse him doing whatever he wants but don't you dare give the same benefits to anyone else.
Chris is obsessed with justifying his actions. A lot of people might do the old drink switcheroo. Either without thinking, or just thinking "meh, it's not a big deal, noone is going to give a shit." I would guess Chris did it for one of those reasons. Even if it is a little bit of a faux-pas, I am not going to get on him for it.
If they are called out on it by an employee, most people would say "Yup, you're right. I won't do it again.", and be a little embarassed about it. Realizing that either through ignorance or through underestimating how much people cared, they had fucked up. If the employee got really angry, some people might even get indignant about that, and say "look, I know I fucked up, but you are really overreacting to a tiny thing."
But Chris is different. He gets called wrong, and he thinks "no, no. I can't be wrong, that is impossible. Let me reexamine this situation to find out why I was right." He uses that type of thinking more than anyone else I know of.
