User defined implicit/explicit conversion operators are an entirely compile time construct. The compiler is going to say something alone the lines of, "Hey, this person is trying to stick a Foo somewhere that expects a Bar. Is a Foo a Bar? No, it's not. Hmm...Oh, I see that Foo has defined an implicit conversion to Bar, I'll go stick in a call to that static conversion method, so that at runtime all of the types match up."
The runtime has no knowledge about implicit/explicit conversions. By the time the program has finished being compiled, those are just regular static methods, like any other static method. Since the compiler only sees conversions from Date
to object
and from object
to Date
, it never sees a place where it needs to add the implicit conversion calls. By the time the runtime gets to it, it only sees that the Date
isn't a DateTime
.