My favorite Rays Place Quote comes from Ray:
Did your mom have on big “clumsy lady” lingerie, all with like a feather boa sewn across the front of the halter, and a large area of thick lace on the front to hide her old lady belly? Man, I don’t even know why I’m askin’ about that. Do me a favor and only read the first sentence of this paragraph. Was her butt pretty long and flat? Was there a long deep line heading down from her bellybutton between some jiggly tummy fat? Man, why do I keep askin' about this stuff?!
This is just great. For certain meanings of "great."
Pontification time: I think that this, like all really good Ray's Place gags, derives its humor both from the letter-writer's pitiful situation and from Ray himself. Here, it's not just funny that we have a ludicrously detailed, icky description of the writer's mom in lingerie; that's funny by itself, but the gag goes from merely "fairly humorous" to "hilarious and a half" by Ray's realization of his own creepiness in asking all this stuff. Ray himself is sort of sick and sad, but -- here's the kicker -- he's still not sick and sad enough for people not to beg his advice.
... so, yeah, Ray's Place is good. Pontification mode off.