>>10
It really does. Lain is one I have shown with much success to anime neophytes who liked movies like Memento or The Usual Suspects.

>>13
I know people who absolutely hated Chobits, so I'm not sure it's as good of an idea as you think. Besides which, for a middle-aged guy (such as the OP is dealing with), the romantic comedy genre might not be the best. Among CLAMP works, xxxHolic might be better for that case.