I notice a pattern - nothing funny Chris has said was intentionally funny and reflects back on himself.
Here's my contribution. On Megan, Chris said:
""Megan, I KNOW you and the PLace employee continuously conversed and conspired against me. "Christian is so weird. " "He hangs onto me, touching me, clinging onto my every word. Ugh."... "I want to just kill him; destroy his goody-two-shoes nature, soul, heart and all that shit my mashed potato grenade could shatter, but leave his body in tact, so I'm not committed for murder.""
That bit in bold... Chris does not understand regular humor, only his own form of humor.
But this is one case where he made an actually-funny joke. The "mashed potato grenade" bit... y'know, because Megan loves the Wehrmacht. And also because of his batshit paranoia about her supposedly hating him and his batshit view of himself as "goody-two-shoes"... It's just like he made a genuinely funny joke about Megan at the same time as making himself look pathetic.