There are asymmetric usages of apologetic expressions in Korea, and those have in common in vocabulary meaning, but also don’t have in common specially in fields of discourse and ritual functions. This study aims at articulating the function's differences about discourse marker and ritual by exploring the data from 15th century to 21th corpus. Given the asymmetric usage of the apologetic expressions, it is necessary to grasp their functions by locating them within larger syntactic structure, such as the conjunctive ending forms, and adjacency pairs. However the functions of these designating apology gradually changed in different discourse contexts, and were replaced by a new conjunctive ending by time.