This paper examines the practical availability and value of expression in Naide-Kudasarudeshouka for various contexts and situations. The speaker is assumedto be a male and the listener to be either [male / female], The personal relationship between the speaker and the listener was classified according to five levels of expressions of politeness: , while the degree of intimacy between the speaker and the listener was grouped into three levels: . The following results were obtained. First, the requisite of Naide-Kudasarudeshouka, was found to be valid in an intimate relationship in which the listener is either of a honorific higher, or equal or higher seniority, or, alternatively, when the listener’s seniority compared to the speaker was undefined. In cases where the speaker and the listener had honorific equal seniorities, or where the listener had a honorific lower seniority compared to the speaker, the politeness implied in deshouka was found to cause estrangement resulting in factitiousness, presenting itself as an estranged relationship in terms of degree of intimacy. This observation would always be valid for estranged relationships, since the interlocutors would not be affected by the politeness implied in deshouka. However, in relationships where the degree of intimacy could be described as undefined, it would not be possible to confirm the aforementioned observation if the speaker and the listener had honorific equal or lower seniorities, or if the speaker had a honorific lower seniority than the listener, because the politeness embedded in deshouka would cause the interlocutors’ psychological distance to be separated, putting them into an estranged relationship. In addition, the paper examined the value of expression satisfied by Naide-Kudasarudeshouka. Naide-Kudasarudeshouka is used in certain contextual, situational conditions in which the speakers’ interpersonal relationship, i.e. the degree of intimacy, is defined as intimate, the expression can assume either one of these values: [solicitation][request] or [anxiety][consideration]. Moreover, when the degree of intimacy is defined as estranged, Naide-Kudasarudeshouka could either represent [unpleasantness][anger] or [rebuke][reprimand] [questioning], causing the politeness implied in deshouka to separate the psychological distance between the two interlocutors, thereby amplifying the speaker’s feeling of unpleasantness or victim mentality. However, in a relationship of undefined intimacy, Naide-Kudasarudeshouka is fundamentally a neutral expression, although the politeness implied in deshouka would amplify the psychological distance between the two interlocutors. It follows that even though this situation could be said tocarry the nuance of unpleasantness, it actually presents itself as an estranged relationship. Generally, Naide-Kudasarudeshouka is known to be used by the person who is in the position of honorific higher seniority compared to their listener, but it is also used in cases in which the speaker is recognized as being at a honorific equal, honorific lower or lower seniority compared to the listener. This tends to occur when the speaker wants to maintain their dignity and reputation by putting distance between themselves to the listener. By considering the relationship and the degree of intimacy between the speaker and the listener in different situations, this research has demonstrated a close connection between the characteristics of the request expression and honorific expressions.